Fast Symptom Glyphosate Formulations

ABSTRACT

Aqueous herbicidal glyphosate compositions are provided, particularly sprayable, ready-to-use (RTU) formulations that are capable of inducing early visually apparent phytotoxic effects while minimizing antagonism to the glyphosate component of the composition and preserving the equally desirable attribute of prolonged control of the treated plants. The compositions combine a glyphosate component and a fatty acid component as a fast symptomology active ingredient and, in one embodiment, are enhanced by the concentration of the fatty acid component utilized and the inclusion of an agronomically acceptable inorganic ammonium salt, preferably ammonium sulfate. In another embodiment, the compositions of the present invention include a nonionic surfactant component comprising certain water-soluble, alkoxylated alcohols.

REFERENCE TO RELATED APPLICATIONS

This application is a division of U.S. patent application Ser. No.11/227,577, filed Sep. 15, 2005, now U.S. Pat. No. 8,268,749, issuedSep. 18, 2012, which claims the benefit of U.S. Provisional ApplicationSer. No. 60/610,695, filed Sep. 17, 2004, the entire contents of whichare incorporated herein by reference.

BACKGROUND OF THE INVENTION

The present invention relates generally to fast-acting herbicidalcompositions or formulations containing glyphosate, and to methods ofusing such compositions to kill or control the growth and proliferationof unwanted plants.

Herbicidal compositions containing the herbicideN-(phosphonomethyl)glycine (commonly referred to as glyphosate) or itsderivatives are useful for killing or suppressing the growth of unwantedplants such as grasses, weeds and the like. The herbicidal properties ofglyphosate and its derivatives were discovered by Franz and patented inU.S. Pat. Nos. 3,799,758 and 4,405,531. Glyphosate herbicidalformulations are typically applied to the foliar tissues (i.e., theleaves or other photosynthesizing organs) of the target plant by sprayapplication. After application, the glyphosate is absorbed by the foliartissues and translocated throughout the plant. Glyphosatenoncompetitively blocks an important biochemical pathway which is commonto virtually all plants, but which is absent in animals. Althoughglyphosate is very effective in killing or controlling the growth ofunwanted plants, the uptake (i.e., absorption) of glyphosate by theplant foliar tissue and translocation of glyphosate throughout the plantis relatively slow. Visually apparent phytotoxic effects or burndownsymptoms (e.g., yellowing, browning, wilting etc.) may not appear untilone week or more after a plant has been treated with glyphosate or itsderivatives.

Given the relatively limited water solubility of the organic acidN-(phosphonomethyl)glycine, aqueous herbicidal compositions aretypically formulated using one or more of the more water-soluble andacceptable salts or other derivatives of glyphosate. Furthermore, thesecompositions typically further contain one or more surfactants toenhance their effectiveness for foliar application. When water is addedto a composition formulated with surfactants, the resulting sprayablecomposition more easily and effectively covers the foliar tissues ofplants. Therefore, glyphosate salts, have been formulated with varioussurfactants such as polyoxyalkylene-type surfactants (e.g., with apolyoxyalkylene alkylamine, and in particular a polyoxyethylenetallowamine). Monsanto Company markets commercial formulations ofglyphosate with such surfactants under the trademark ROUNDUP.

Nevertheless, because of the somewhat slow development of visualsymptoms of plant suppression or death that result when glyphosate isutilized alone or even with a surfactant, various alternative herbicidalformulations have been suggested to induce earlier visual symptoms oftreatment. Early symptom-producing or fast-acting, ready-to-use (RTU)compositions are particularly desired in the lawn and garden marketwhere the consumer appreciates relatively immediate evidence that theproduct is having the desired effect.

Attempts at inducing earlier visual symptomology have included combiningglyphosate or its derivatives with certain fatty acids or theirherbicidally active salts, for example, pelargonic acid (PA; alsoreferred to as nonanoic acid), capric acid (also referred to as decanoicacid) and mixtures of such fatty acids or salts thereof as described,for example, in U.S. Pat. Nos. 5,196,044 (Caulder, et al.) and 5,994,269(Bugg, et al.), International Publication No. WO 92/07467, EuropeanPatent Application Publication No. 0 577 914, and by Kristin A. Arnold,et al. in “Improved Early Symptom Development with a Ready-To-UseGlyphosate Formulation by Addition of Fatty Acid,” Pesticide Science,38(2-3), pp. 270-272 (1993). It is suggested that such a combinationprovides a herbicidal formulation capable of inducing fast symptomologyin the treated plants due to the fatty acid component and prolongedcontrol due to the glyphosate component. Indeed some success has beenachieved along these lines in RTU formulations available from MonsantoCompany and other manufacturers.

However, despite some degree of success in providing herbicidalcompositions that accelerate the appearance of visual phytotoxiceffects, there remains a need, particularly in the RTU market segment,for improved glyphosate formulations providing even faster symptomology.Moreover, previous attempts, while inducing earlier visual effects ontreated plants, have sometimes suffered from less than expected ordesired long-term control, perhaps due to unintended antagonism to theglyphosate component by other ingredients of the herbicidal composition.Still further, difficulty has been encountered in providing fast-actingglyphosate compositions that resist separation of the active ingredientsand other components of the formulation from the aqueous solution uponprolonged storage and that can be readily formulated as a concentrate.

SUMMARY OF THE INVENTION

Among the objects of the present invention, therefore, are the provisionof aqueous herbicidal glyphosate compositions capable of inducing earlyappearance of visual phytotoxic effects in treated plants; the provisionof such compositions exhibiting overall superior herbicidal activity andlong-term control of unwanted plants; the provision of such compositionsin which antagonism to long-term control of unwanted plants by theglyphosate component of the composition is reduced or eliminated; theprovision of such aqueous herbicidal glyphosate compositions that may bereadily formulated as a concentrate or as a sprayable ready-to-use (RTU)product; the provision of such compositions that are resistant toseparation of the components of the formulation from the aqueoussolution upon prolonged storage; and the provision of methods forkilling or controlling the growth of a broad spectrum of unwanted plantsspecies by applying to the foliar tissues of the plants aqueousherbicidal glyphosate compositions of the present invention.

Briefly, therefore, the present invention is directed to an aqueousready-to-use herbicidal composition useful for killing or controllingthe growth of unwanted plants. The RTU composition comprises from about0.1% to about 5% by weight acid equivalent (a.e.) of a glyphosatecomponent comprising N-(phosphonomethyl)glycine, an agronomicallyacceptable salt of N-(phosphonomethyl)glycine or a mixture thereof; atleast about 1.5% and up to about 5% by weight (a.e.) of a fatty acidcomponent predominantly comprising at least one C₈ to C₁₂ saturated,straight or branched chain fatty acid or an agronomically acceptablesalt thereof; and from about 0.5% to about 4% by weight of anagronomically acceptable inorganic ammonium salt.

In accordance with another embodiment of the invention, the aqueous RTUherbicidal composition comprises from about 0.1% to about 5% by weight(a.e.) of a glyphosate component comprising N-(phosphonomethyl)glycine,an agronomically acceptable salt of N-(phosphonomethyl)glycine or amixture thereof; from about 0.25% to about 5% by weight (a.e.) of afatty acid component predominantly comprising at least one C₈ to C₁₂saturated, straight or branched chain fatty acid or an agronomicallyacceptable salt thereof; and from about 1% to about 4% by weight ofammonium sulfate.

In accordance with one preferred embodiment, the aqueous RTU herbicidalcomposition comprises from about 1% to about 5% by weight (a.e.) of aglyphosate component predominantly comprising a salt ofN-(phosphonomethyl)glycine selected from the isopropylammonium salt ofN-(phosphonomethyl)glycine, the ammonium salt ofN-(phosphonomethyl)glycine and the potassium salt ofN-(phosphonomethyl)glycine; at least about 1.5% and up to about 3% byweight (a.e.) of a fatty acid component predominantly comprisingpelargonic acid or an agronomically acceptable salt thereof; and fromabout 1.5% to about 3% by weight of ammonium sulfate.

The present invention is further directed to an aqueous herbicidalcomposition useful for killing or controlling the growth of unwantedplants comprising a glyphosate component comprisingN-(phosphonomethyl)glycine, an agronomically acceptable salt ofN-(phosphonomethyl)glycine or a mixture thereof; a fatty acid componentcomprising at least one saturated or unsaturated, straight or branchedchain C₅ to C₁₈ fatty acid or agronomically acceptable salt thereof; anda nonionic surfactant (NIS) component comprising an alkoxylated, C₈ toC_(H), nonaromatic alcohol with an average degree of alkoxylation suchthat the alcohol has a solubility in water of at least about 0.5% byweight at 25° C.

In accordance with another embodiment of the present invention, theaqueous herbicidal composition including a nonionic surfactant componentcomprising an alkoxylated, C₈ to C₂₀, nonaromatic alcohol is prepared inthe form of an RTU composition. In one such preferred embodiment, theaqueous RTU herbicidal composition comprises from about 0.1% to about 5%by weight (a.e.) of a glyphosate component predominantly comprising asalt of N-(phosphonomethyl)glycine selected from the isopropylammoniumsalt of N-(phosphonomethyl)glycine, the ammonium salt ofN-(phosphonomethyl)glycine and the potassium salt ofN-(phosphonomethyl)glycine; from about 0.25% to 5% by weight (a.e.) of afatty acid component predominantly comprising pelargonic acid or a saltthereof; from about 0.5% to about 12% by weight of the nonionicsurfactant component predominantly comprising ethoxylated, primary orsecondary, undecyl alcohol with an average degree of ethoxylation offrom about 5 to about 9; and from about 0.5% to about 4% by weight ofammonium sulfate.

The present invention is further directed to methods for killing orcontrolling the growth of unwanted plants, comprising treating the plantby applying to the foliar of the plant an aqueous herbicidal compositionin accordance with the present invention.

Other objects and features of this invention will be in part apparentand in part pointed out hereinafter.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

In accordance with the present invention, aqueous herbicidal glyphosatecompositions are provided, particularly sprayable, ready-to-use (RTU)formulations that are capable of inducing early, visually apparent,phytotoxic effects while minimizing antagonism to the glyphosatecomponent of the composition and preserving the equally desirableattribute of prolonged control of the treated plants. These formulationsare based in part on the previously identified combination of a fattyacid component as a fast symptomology active ingredient with aglyphosate component capable of providing long-term control of thetreated plants. However, in accordance with a first aspect of thepresent invention, consistent fast symptomology and overall herbicidaleffectiveness are enhanced by the concentration of the fatty acidcomponent utilized and the inclusion of an agronomically acceptableinorganic ammonium salt, preferably ammonium sulfate. By employingappreciable quantities of the fatty acid component and ammonium sulfateor other inorganic ammonium salt, a formulation is provided that furtheraccelerates or otherwise enhances visually apparent phytotoxic effectsin the treated plants. Although use of a surfactant in the compositionsof the present invention is not required, use of a surfactant ispreferred and, in accordance with a further aspect of the invention, ithas been discovered that faster symptomology in the treated plants canbe achieved by the inclusion of a nonionic surfactant componentcomprising certain water-soluble, alkoxylated alcohols. The presentinvention contemplates and provides sprayable aqueous glyphosate RTUcompositions in which the components resist separation from the aqueoussolution even upon prolonged storage and are suitable for formulation asa concentrate.

The herbicidal compositions of the present invention are applied asaqueous solutions or dispersions. However, the term “aqueous,” as usedherein, is not intended to exclude the presence of nonaqueous (i.e.,organic) solvents, as long as water is present. Water is the predominantcomponent of the aqueous RTU compositions disclosed herein.

The glyphosate component of the aqueous composition is typicallyprimarily responsible for plant suppression or death and is instrumentalin imparting long-term herbicidal control. The glyphosate componentcomprises N-(phosphonomethyl)glycine, a salt or other agronomicallyacceptable derivative of N-(phosphonomethyl)glycine which is convertedto glyphosate in plant tissues or which otherwise provides glyphosateanion or a mixture thereof. In this regard it is to be noted that theterm “glyphosate” or “glyphosate component” when used herein isunderstood to encompass N-(phosphonomethyl)glycine, such derivatives aswell as mixtures thereof unless the context requires otherwise.Furthermore, the term “agronomically acceptable” includes glyphosatederivatives that allow agriculturally and economically useful herbicidalactivity of an N-(phosphonomethyl)glycine anion in residential orindustrial applications.

In the aqueous herbicidal compositions of the present invention, it ispreferred that the glyphosate component predominantly comprise one ormore of the more water-soluble salts of N-(phosphonomethyl)glycine. Asused throughout this specification, the expression “predominantlycomprises” means more than 50%, preferably at least about 75%, and morepreferably at least about 90% by weight of the component of theherbicidal composition is made up of the specified compound(s). Aglyphosate component predominantly comprising one or more of the varioussalts of N-(phosphonomethyl)glycine is preferred in part because theirincreased water solubility that allows formulation of highlyconcentrated herbicidal compositions that can be easily transported andreadily diluted with water in the preparation of sprayable RTUcompositions at the site of intended use.

Suitable salts of N-(phosphonomethyl)glycine include mono-, di- ortribasic and include organic ammonium, alkali metal, alkaline earthmetal, ammonium (e.g., mono-, di- or triammonium) and sulfonium (e.g.,mono-, di- or trimethylsulfonium) salts of N-(phosphonomethyl)glycine.The organic ammonium salts can comprise aliphatic or aromatic ammoniumsalts and can include primary, secondary, tertiary or quaternaryammonium salts. Specific representative examples of such organicammonium salts include isopropylammonium, n-propylammonium,ethylammonium, dimethylammonium, 2-hydroxyethylammonium (also referredto as monoethanolammonium), ethylenediamine and hexamethylenediaminesalts of N-(phosphonomethyl)glycine. Specific representative examples ofalkali metal salts include potassium and sodium salts ofN-(phosphonomethyl)glycine. In accordance with a more preferredembodiment of the invention, the glyphosate component predominantlycomprises a salt of N-(phosphonomethyl)glycine selected from thepotassium, monoammonium, diammonium, sodium, monoethanolammonium,n-propylammonium, isopropylammonium, ethylammonium, dimethylammonium,ethylenediamine, hexamethylenediamine and trimethylsulfonium salts andcombinations thereof. Of these, the isopropylammonium, ammonium andpotassium salts and combinations thereof are especially preferred.

The concentration of the glyphosate component in aqueous RTUcompositions of the present invention is typically at least about 0.1%and generally from about 0.1% to about 5% by weight acid equivalent(a.e.). However, it has been observed that reduced antagonism tolong-term herbicidal control (i.e., reduction in glyphosate performance)is achieved when the concentration of the glyphosate component in theRTU formulation is at least about 1% by weight (a.e.). Accordingly, theconcentration of the glyphosate component in the RTU composition ispreferably from about 1% to about 5% by weight (a.e.). In order toprovide more economical RTU formulations providing prolonged herbicidalactivity, the concentration of the glyphosate component in the RTUcomposition is more preferably from about 1% to about 2% by weight(a.e.), even more preferably from about 1.25% to about 2% by weight(a.e.) and optimally about 1.5% by weight (a.e.).

While ROUNDUP herbicide is a suitable source of water-soluble glyphosatesalt, other formulations providing a water-soluble glyphosate salt orN-(phosphonomethyl)glycine may be employed as a starting material.Alternatively, a water-soluble glyphosate salt or an aqueous solutionthereof may be prepared prior to or during the formulation of theaqueous herbicidal composition by neutralizingN-(phosphonomethyl)glycine with an appropriate base to form thecorresponding salt. For example, N-(phosphonomethyl)glycine may be usedas a starting material and partially or fully neutralized along with thefatty acid or fatty acid mixture of the fatty acid component duringformulation of an aqueous RTU herbicidal composition.

The fatty acid component of the aqueous herbicidal composition assistsin imparting rapid symptomology and more consistent herbicidal controlto the composition. The fatty acid component comprises at least onesaturated or unsaturated, straight or branched chain C₅ to C₁₈ fattyacid, salt, ester or other agronomically acceptable derivative thereofand can be, for example, in the epoxide, cyclopropane, methylated orhydroxylated forms. The fatty acid component may comprise various alphamonocarboxylic fatty acids such as caprylic acid (C₈), pelargonic acid(C₉), capric acid (C₁₀), undecanoic acid (C₁₁), lauric acid (C₁₂),palmitic acid (C₁₆), stearic acid, oleic acid, linoleic acid andlinolenic (all C₁₈), their salts and mixtures thereof. Furthermore, thefatty acid component may be derived from naturally occurring oilscontaining fatty acid mixtures such as soybean fatty acids and coconutfatty acids and salts of such mixtures.

Suitable fatty acids, fatty acid derivatives and mixtures thereof aredisclosed, for example, in U.S. Pat. Nos. 5,098,468 (Puritch, et al.),5,106,410 (Puritch, et al.), 5,196,044 (Caulder, et al.), 5,994,269(Bugg, et al.) and 6,930,075 (Mason), European Patent ApplicationPublication No. 0 577 914, and International Publication No. WO89/03178, the entire disclosures of which are incorporated herein byreference.

Preferably, the fatty acid component of the herbicidal compositionpredominantly comprises at least one C₈ to C₁₂ saturated, straight orbranched chain fatty acid (e.g., caprylic acid, pelargonic acid, capricacid, undecanoic acid or lauric acid) or agronomically acceptable saltthereof. Various partial or complete salts of fatty acids or fatty acidmixtures may be used in the fatty component. Essentially anyagronomically acceptable salt of the fatty acid or fatty acid mixturemay be utilized in the practice of the present invention. Fatty acidsand fatty acid mixtures may be neutralized with bases of various typesto form the corresponding salt either prior to or during formulation ofthe aqueous herbicidal composition. For example, as described below, thefatty acid component may be partially or fully neutralized with a pHadjuster (e.g., potassium hydroxide) used to adjust the pH of an RTUcomposition during formulation. Suitable fatty acid salts includeammonium salts, alkali metal salts (e.g., potassium and sodium salts),alkaline earth metal salts of the fatty acid or fatty acid mixture aswell as mixtures of such salts. Preferably, the fatty acid salts used inthe practice of the present invention include the potassium and sodiumsalts of the fatty acid or fatty acid mixture.

In an especially preferred embodiment, the fatty acid component of theherbicidal composition predominantly comprises pelargonic acid or anagronomically acceptable salt thereof. More preferably still, the fattyacid component comprises at least about 90% by weight pelargonic acid oran agronomically acceptable salt thereof. Among the most preferred fattyacid salts are sodium and potassium pelargonate. Commercially availablesources of pelargonic acid typically comprise a mixture of pelargonicacid with other fatty acids such as caprylic acid and capric acid,however, pelargonic acid nevertheless typically predominates.Commercially available sources of pelargonic acid include the productssold as AGNIQUE FAC 9 and EMERY 1202 by Cognis Corporation (Cincinnati,Ohio) and n-pelargonic acid available from Celanese Limited (Dallas,Tex.).

In accordance with one embodiment of the present invention, anagronomically acceptable inorganic ammonium salt is optionally combinedwith the glyphosate component and fatty acid component of the aqueousherbicidal composition. The ammonium salt, in conjunction with the fattyacid component, further accelerates the appearance of visual phytotoxiceffects in the treated plants and enhances overall herbicidal efficacy.Suitable inorganic ammonium salts include ammonium sulfate, ammoniumnitrate, ammonium thiocyanate, ammonium phosphate, ammonium chloride andmixtures thereof. Ammonium sulfate is particularly effective in inducingearly symptomology in treated plants and for that reason is especiallypreferred for inclusion in the compositions of the present invention.

The aqueous herbicidal RTU compositions of the present inventiontypically contain at least about 0.25% by weight acid equivalent (a.e.)of the fatty acid component and, when utilized, at least about 0.5% byweight of the inorganic ammonium salt(s). Generally, RTU formulationscontain from about 0.25% to about 5% by weight (a.e.) of the fatty acidcomponent and from about 0.5% to about 4% by weight of the inorganicammonium salt. However, early onset of phytotoxic effects in treatedplants is enhanced, particularly in RTU formulations containing ammoniumsulfate, when the concentration of the inorganic ammonium salt(s) andthe fatty acid component (a.e.) are independently at least about 1%,preferably at least about 1.5% and especially at least about 2% byweight. Accordingly, the aqueous RTU formulation preferably comprisesfrom about 1% to about 4%, more preferably from about 1.5% to about 3%and optimally about 2% by weight of ammonium sulfate or other inorganicammonium salt(s) along with significant quantities of the fatty acidcomponent, preferably at least about 1% and up to about 5%, morepreferably at least about 1.5% and up to about 5%, even more preferablyat least about 1.5% and up to about 3% and optimally about 2% by weight(a.e.) of the fatty acid component.

In addition to water, the glyphosate component, fatty acid component andoptional inorganic ammonium salt, aqueous herbicidal compositions inaccordance with the present invention may further comprise one or moreoptional adjuvants (e.g., surfactant), excipients, additional activeherbicidal ingredients or other additives. Greater or lesser amounts ofthese optional ingredients may be employed as desired.

Although not required in the practice of the present invention, theaqueous herbicidal RTU compositions of the present invention preferablyoptionally include a surfactant component comprising one or moresurfactants. Various cationic and nonionic surfactants known to enhancethe effectiveness of post-emergent herbicides such as glyphosate byfacilitating foliar contact with the herbicide and subsequenttranslocation, as well as mixtures of such surfactants, may be used informulating the aqueous herbicidal compositions. A general requirementof suitable surfactants is adequate water and fat solubility to permitdissolution of the herbicide active ingredients and interaction of thedissolved herbicides with waxy foliar tissues when applied to plants.Generally, the surfactant component should be water-soluble and compriseone or more surfactants characterized by a solubility of at least about0.5% by weight in water at 25° C.

Examples of the types of suitable surfactants and surfactant mixturesthat may be used in the practice of the present invention includealkylamine ethoxylates and combinations of an alkylamine ethoxylate andalkylethoxylate phosphate or sulfonate ester, alkylamine oxides, alkylglucosides, alkoxylated (e.g., ethoxylated or propoxylated) quaternaryamines, dialkylacetylenes, etheramine alkoxylates, quaternary etheraminealkoxylates, trimethyl alkylammonium chlorides, trimethyl etherammoniumchlorides and water-soluble, nonionic surfactants such as alcoholalkoxylates and alkylphenol alkoxylates (e.g., alkoxylated nonylphenol).

Specific examples of these types of surfactants and surfactantcombinations include a blend of tallowamine ethoxylate having an averagedegree of ethoxylation of about 10 with an alkylethoxylate phosphateester in polyethylene glycol (500 average molecular weight), dipropyleneglycol and water solvents; and tallowamine ethoxylate having an averagedegree of ethoxylation of about 10.5 in dipropylene glycol solvent.

In accordance with one embodiment of the present invention, a nonionicsurfactant component comprising one or more selected water-soluble,nonionic surfactants is combined with the glyphosate component and fattyacid component of the aqueous herbicidal RTU composition. Moreparticularly, it has been discovered that a nonionic surfactantcomponent comprising certain alkoxylated alcohols enhance the ability ofthe fatty acid component and the inorganic ammonium salt (e.g., ammoniumsulfate), if present, to induce early visual phytotoxic effects intreated plants.

In such an embodiment, the nonionic surfactant component comprises analkoxylated, C₈ to C₂₀, nonaromatic alcohol with a sufficient averagedegree of alkoxylation such that the alkoxylated alcohol has asolubility in water of at least about 0.5% by weight at 25° C. Each ofthe alkoxy groups independently comprises C₂ to C₄ alkylene, preferablyethylene or propylene, and the average degree of alkoxylation (e.g.,ethoxylation) is typically from about 2 to about 20, preferably fromabout 3 to about 12, and more preferably from about 5 to about 9.

The preferred nonionic surfactants include alkoxylated alcohols havingthe formula:

R¹O—(R²O)_(x)R³

wherein R¹ is nonaromatic, hydrocarbyl or substituted hydrocarbyl havingfrom 8 to 20 carbon atoms, R² in each of the x (R²O) groups isindependently C₂ to C₄ alkylene, R³ is hydrogen, or a linear or branchedalkyl group having from 1 to about 4 carbon atoms, and the averagedegree of alkoxylation, x, is from about 2 to about 20. It has beenobserved that alkoxylated aromatic alcohols (e.g., alkoxylatednonylphenol) and highly branched, alkoxylated alcohols (e.g.,alkoxylated isotridecyl alcohol) are not particularly useful inenhancing early visual phytotoxic effects in treated plants.Accordingly, in this context, it is preferred that the nonionicsurfactant comprise an alkoxylated, primary or secondary, linear orminimally branched (i.e., acyclic) C₈ to C₂₀, preferably C₁₀ to C₁₄,alcohol such that the preferred R¹ hydrocarbyl groups are linear orminimally branched alkyl, alkenyl or alkynyl groups having from 8 to 20carbon atoms, preferably from 10 to 14 carbon atoms, and no more thantwo methyl substituents. Preferably, R¹ is a linear or minimallybranched alkyl or alkenyl group having from 8 to 20 carbon atoms,preferably from 10 to 14 carbon atoms, and no more than two methylsubstituents, R² in each of the x (R²O) groups is independently ethyleneor propylene, preferably ethylene, R³ is hydrogen, methyl or ethyl, andthe average degree of alkoxylation (e.g., ethoxylation), x, is fromabout 3 to about 12, more preferably from about 5 to about 9. Morepreferably, R¹ is a linear or minimally branched alkyl group having from8 to 20 carbon atoms, preferably from 10 to 14 carbon atoms, and no morethan two methyl substituents, R² in each of the x (R²O) groups isethylene, R³ is hydrogen or methyl, and the average degree ofethoxylation, x, is from about 3 to about 12, more preferably from about5 to about 9.

Examples of suitable commercially available alkoxylated, linear alcoholsfor use in the nonionic surfactant component include alcohol ethoxylatessold under the name TOMADOL by Tomah, Products Inc. (Milton, Wis.) andincluding TOMADOL 25-3, TOMADOL 25-7 and TOMADOL 25-9 (made from linearC₁₂ to C₁₅ alcohols with an average of 2.8 moles, 7 moles and 9 moles ofethoxylation, respectively). Other commercially available alkoxylated,linear alcohols that may be used in the nonionic surfactant componentare those in the TERGITOL series from Dow and commercially availablefrom Sigma-Aldrich Co. (Saint Louis, Mo.), including TERGITOL-15-S-9,TERGITOL-15-S-12 and TERGITOL-15-S-15 (made from secondary, linear C₁₁to C₁₅ alcohols with an average of 9 moles, 12.3 moles and 15.5 moles ofethoxylation, respectively); and the SURFONIC LF-X series from HuntsmanChemical Co. (Salt Lake City, Utah), including L12-7 (made from linearC₁₀ to C₁₂ alcohols with an average of 7 moles of ethoxylation), L24-7,L24-9 and L24-12 (made from linear C₁₂ to C₁₄ alcohols with an averageof 7 moles, 9 moles and 12 moles of ethoxylation, respectively), andL26-6.5 (made from linear C₁₂ to C₁₆ alcohols with an average of 6.5moles of ethoxylation).

In accordance with one preferred embodiment of the present invention,the nonionic surfactant component predominantly comprises ethoxylated,primary or secondary, undecyl alcohol with an average degree ofethoxylation of from about 3 to about 12, more preferably from about 5to about 9. More preferably, the ethoxylated undecyl alcohol thatpredominates the nonionic surfactant component is an ethoxylated,primary, linear undecyl alcohol. Examples of such preferred ethoxylated,linear undecyl alcohols include TOMADOL 1-3 (average of 3 moles ofethoxylation), TOMADOL 1-5 (average of 5 moles of ethoxylation) andTOMADOL 1-9 (average of 9 moles of ethoxylation). In accordance with anespecially preferred embodiment, the nonionic surfactant component ofthe aqueous herbicidal composition comprises at least about 90% byweight ethoxylated, primary, linear undecyl alcohol having an averagedegree of ethoxylation of about 7. An example of such an especiallypreferred ethoxylated, primary, linear undecyl alcohol is TOMADOL 1-7(average 7 moles of ethoxylation). BEROL 537 and ETHYLAN 1008 from AkzoNobel (Chicago, Ill.) are similar to TOMADOL 1-7, both being made fromlinear C₁₁ alcohols with an average of about 7 moles of ethoxylation.

The nonionic alkoxylated alcohol surfactant component as described abovemay be combined with other suitable surfactants and surfactantcombinations such as those disclosed herein. However, it has beenobserved that combining such a nonionic surfactant with a cationicsurfactant (e.g., a tallowamine ethoxylate) tends to compromise the fastdevelopment of symptoms in treated plants. Accordingly, in one preferredembodiment, the surfactant component of the aqueous RTU herbicidalcomposition consists essentially of an alkoxylated, nonaromatic alcoholnonionic surfactant or a mixture of such nonionic surfactants. In anyevent, it should be understood that surfactants are optional in thecompositions of the present invention and can be omitted entirely andreplaced by water.

When utilized, an effective concentration of the surfactant component inthe aqueous RTU compositions can be readily determined by those skilledin the art and may vary within wide limits depending upon the type(s) ofsurfactants employed, the other ingredients present in the compositionand the targeted herbicidal efficacy with respect to the plants to betreated. Generally, the RTU composition may contain at least about 0.5%by weight of a surfactant component. For example, in the case of asurfactant component comprising an alkylamine ethoxylate or combinationsof an alkylamine ethoxylate and alkylethoxylate phosphate ester in aglycol solvent, a concentration of up to about 1% by weight may besuitably employed. However, in the case of the nonionic surfactantcomponent comprising an alkoxylated, nonaromatic alcohol, generallyslightly higher concentrations are preferred. Preferably, theconcentration of the nonionic surfactant component in the RTUcomposition is from about 0.5% to about 12% by weight, more preferablyfrom about 0.5% to about 5% by weight.

Examples of additional herbicidal active ingredients that may beincluded in the herbicidal compositions include, without limitation,water-soluble forms of phenoxy herbicides such as(2,4-dichlorophenoxy)acetic acid (2,4-D),4-(2,4-dichlorophenoxy)butanoic acid (2,4-DB) and(4-chloro-2-methylphoenoxy)acetic acid (MCPA), as well as dicamba,diquat bromide, glufosinate, imazapic, imazapyr, imazethapyr, triclopyrand mixtures thereof. Additional herbicidal active ingredients alsoinclude forms of these herbicides that are not readily water-soluble(e.g., an ester form of a phenoxy herbicide), that are coupled into theaqueous herbicidal composition by inclusion of a sufficient quantity ofan appropriate surfactant. In addition, the compositions of the presentinvention may include finely-divided, water-insoluble herbicides, forexample, triazines, substituted ureas (e.g., diuron), sulfonylureas,diphenyl ethers, dinitroanilines, pryidines, oxyfluorfen, oryzalin andthe like. Additional herbicidal active ingredient(s) in an RTUformulation are present in an agriculturally useful concentration thatwill vary depending on the particular additional herbicide(s) selectedfor inclusion and is readily determined by those skilled in the art.

The herbicidal compositions may further comprise other conventionaladjuvants, excipients or additives known to those skilled in the art.These other additives or ingredients may be introduced into thecompositions of the present invention to provide or improve certaindesired properties or characteristics of the formulated product. Hence,the herbicidal composition may further comprise one or more additionalingredients selected from, without limitation, foam-moderating agents,preservatives or anti-microbials, antifreeze agents,solubility-enhancing agents, dyes, pH adjusters and thickening agents.

Suitable foam-moderating agents include silicone-based compositions. Anexample of a foam-moderating agent for RTU compositions is SAG-10,available from GE Silicones Corporation (Wilton, Conn.). The amount offoam-moderating agent optionally employed is that which is sufficient toinhibit and/or reduce an amount of foam that may otherwise be formedduring the process of preparing and containerizing the formulationand/or use thereof to a desired and satisfactory level. Generally, inthe case of RTU compositions, the concentration of foam-moderating agentis in the range from about 0.001% up to about 0.05% by weight of thecomposition, and typically from about 0.01% to about 0.03% by weight ofthe composition, although greater or lesser amounts may be employed.

The compositions may also comprise a preservative such as PROXEL GXLcontaining 1,2-benzisothiazolin-3-one (CAS No. 2634-33-5) available fromAvecia, Inc. (Wilmington, Del.), DOWICIL 150 containingcis-1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadmatane chloride (CAS No.051229-78-8) available from Dow Chemical Company (Midland, Mich.),NIPACIDE BIT20DPG containing benzisothiazolinone available from ClariantCorporation (Greensboro, N.C.), LEGEND MK anti-microbial biocideavailable from Rohm and Haas Co. (Philadelphia, Pa.), sorbic acid,mixtures thereof and the like in the range of from about 0.01% to about0.2% by weight, preferably about 0.1% by weight of the RTU composition.

Suitable antifreeze agents include ethylene glycol and propylene glycoland generally may be present at a concentration of from about 0.1% toabout 10% by weight of the RTU composition. Antifreeze agents assist inlowering the freezing point of aqueous solutions and maintainingsolubility of the components of the composition such that components donot crystallize or precipitate during cycles of freezing and thawing.

Although the RTU compositions of the present invention generally showgood overall stability and viscosity properties without the addition ofany further additives, the addition of a solubility-enhancing agent(also commonly referred to as a cloud point enhancer or stabilizer) maysignificantly improve the properties of the formulations.Solubility-enhancing agents include polymer derivatives of ethyleneglycol and propylene glycol (e.g., 200-1200 average molecular weight),glycerol, sugars, mixtures thereof and the like in amounts up to about10%, preferably from about 0.05 to about 10% by weight, more preferablyfrom about 0.1 to about 1% by weight of the RTU composition.

The herbicidal RTU compositions of the present invention can be readilyprepared by simple mixing of the various components and optionalingredients in the desired quantities using a mechanical stirrer or anyother suitable container or device producing the necessary amount ofagitation or circulation to thoroughly mix the ingredients. The order ofaddition of the starting materials is not critical. For example, anherbicidal RTU composition may be formulated by first dissolvingammonium sulfate or other optional inorganic ammonium salt in water,adding the glyphosate component and optional surfactant component,followed by addition of potassium hydroxide or other suitable strongbase and then addition of the fatty acid component. Although noparticular mixing or formulating technique is required, generalreference may be made to the formulation preparation process disclosedin U.S. Pat. No. 5,994,269 (Bugg, et al.), the disclosure of which isincorporated herein by reference.

In the practice of the present invention, the pH of the herbicidalcomposition is preferably controlled in order to obtain a storage stableformulation and one that effectively provides the desired fastdeveloping symptomology. More particularly, in some embodiments, thefinal pH of the herbicidal RTU composition is preferably controlled inthe range of from about 7.1 to about 7.6. If the pH of the finalcomposition is below about 7.1, the fatty acid component may tend toseparate from the composition upon standing and it may be necessary forthe user to shake or agitate the composition to obtain a uniformsolution to spray. However, if the final pH is greater than about 7.6,the development of symptoms in treated plants may be undesirablydelayed. Accordingly, there is a balance to be achieved between thesetwo considerations. In accordance with a more preferred embodiment ofthe invention, the final pH of the RTU composition is controlled in therange of from about 7.2 to about 7.5, even more preferably, from about7.25 to about 7.4 and especially at about 7.3.

However, in accordance with some embodiments of the present invention,it has been discovered that the adverse effect of higher pH on earlydevelopment of symptomology discussed above is substantially diminishedif the herbicidal composition includes an inorganic ammonium salt suchas ammonium sulfate, preferably in combination with a nonionicsurfactant such as an alkoxylated nonaromatic alcohol. Hence, in such anembodiment, suitable results are nevertheless attained when thecomposition exhibits a final pH in excess of about 7.6, in excess ofabout 7.7, in excess of about 7.8, in excess of about 7.9 and even up toabout 8. Preferably, herbicidal composition including an inorganicammonium salt in combination with a nonionic surfactant have a pH offrom about 7.1 to about 8 and more preferably from about 7.2 to about7.8. Thus, the combination of an inorganic ammonium salt and nonionicsurfactant in the herbicidal compositions of the present inventionprovides the further advantage of widening the acceptable pH range inthe formulated product to provide greater ease and flexibility in theformulation manufacturing process.

If pH adjustment is necessary, it is readily achieved by the addition ofpH adjusting base or acidic component such as additional fatty acid orglyphosate component during the formulation preparation process.Suitable bases for pH adjustment include those providing hydroxide inwater, preferably an amine or alkali metal or alkaline earth metalhydroxide, and most preferably potassium hydroxide.

The formulation may be filtered (or other equivalent means employed) toremove any insoluble particulate impurities that may be present in someof the ingredients employed (e.g., commercial grades of ammoniumsulfate).

The preceding description has focused primarily on aqueous RTUherbicidal compositions provided to the end-user already formulated atthe desired dilution and ready for application to the foliage ofunwanted plants. However, the herbicidal compositions may alternativelybe prepared as concentrates suitable for later dilution in water toobtain a formulation having a composition desired for application.Concentrate formulations permit economy and ease of transportation, forexample, from manufacturing site to the site of use.

In the formulation of aqueous concentrate compositions, theconcentration of the glyphosate component, fatty acid component and thevarious optional ingredients are generally higher than as previouslydescribed with respect to the RTU formulations. However, as described ingreater detail below, it may be advantageous to utilize additional oralternative surfactants, surfactant combinations or solubility-enhancingagents and/or to adjust the relative proportions of the variouscomponents of the concentrate in order to attain a stable concentratesolution.

In the preparation of concentrates, a glyphosate component predominantlycomprising a salt of N-(phosphonomethyl)glycine, particularly theisopropylammonium salt, ammonium salt, potassium salt or combinationsthereof, is preferred in order to take advantage of the high watersolubility that facilitate the formulation of highly concentratedherbicidal compositions. Accordingly, there is no practical limitationon the concentration of the glyphosate component in concentrateformulations. The glyphosate component is typically at least about 5% byweight (a.e.), preferably in the range from about 5% to about 25% byweight (a.e.), more preferably from about 10% to about 20% by weight(a.e.) and even more preferably from about 12% to about 18% by weight(a.e.) of the concentrate formulation.

Due to the somewhat limited solubility characteristic of pelargonic acidas well as other fatty acids and derivatives and the optional inorganicammonium salt at higher concentrations in aqueous formulations, whenformulating concentrates, it may be advantageous to employ higherproportions of a surfactant component and/or surfactants or surfactantcombinations different from those used in the preparation of RTUformulations and adapted to maintain sufficient solubility of thevarious components. Examples of the types of suitable surfactants andsurfactant combinations that may be used in the surfactant componentwhen formulating concentrate compositions of the present inventioninclude the previously described nonionic surfactant componentcomprising an alkoxylated nonaromatic alcohol, preferably combined withadditional surfactants to enhance stability of the concentrate. Examplesof suitable stability enhancing surfactants that may be used eitheralone or in combination with the nonionic alkoxylated nonaromaticalcohol surfactants include alkyl polyglucosides (APGs), anddialkoxylated quaternary ammonium salt surfactants having the formula:

wherein R¹ is hydrocarbyl or substituted hydrocarbyl having from 1 toabout 30 carbon atoms, R² in each of the x (R²O) and y (R²O) groups isindependently C₂-C₄ alkylene, R³ is hydrogen, or a linear or branchedalkyl group having from 1 to about 4 carbon atoms, R⁴ is hydrogen orhydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbonatoms, x and y are independently an average number from 1 to about 40,and X⁻is an agronomically acceptable anion. In this context, preferredR¹ and R⁴ hydrocarbyl groups are linear or branched alkyl, linear orbranched alkenyl, linear or branched alkynyl, aryl, or aralkyl groups.Preferably, R¹ and R⁴ are independently a linear or branched alkyl orlinear or branched alkenyl group having from 1 to about 25 carbon atoms,R² in each of the x (R²O) and y (R²O) groups is independently C₂-C₄alkylene, R³ is hydrogen, methyl or ethyl, and the sum of x and y is anaverage number from about 2 to about 30. More preferably, R¹ and R⁴ areindependently a linear or branched alkyl group having from 1 to about 22carbon atoms, R² in each of the x (R²O) and y (R²O) groups isindependently ethylene or

propylene, R³ is hydrogen or methyl, and the sum of x and y is anaverage number from about 2 to about 20. Even more preferably, R¹ is alinear or branched alkyl group having from about 8 to about 22 carbonatoms and R⁴ is a linear or branched alkyl group having from 1 to about22 carbon atoms, R² in each of the x (R²O) and y (R²O) groups isindependently ethylene or propylene, R³ is hydrogen or methyl, and thesum of x and y is an average number from about 2 to about 20. Mostpreferably, R¹ is a linear or branched alkyl group having from about 8to about 22 carbon atoms and R⁴ is a linear or branched alkyl grouphaving from 1 to about 6 carbon atoms, R² in each of the x (R²O) and y(R²O) groups is independently ethylene or propylene, R³ is hydrogen ormethyl, and the sum of x and y is an average number from about 2 toabout 15, or R¹ and R⁴ are independently a linear or branched alkylgroup having from about 8 to about 22 carbon atoms, R² in each of the x(R²O) and y (R²O) groups is independently ethylene or propylene, R³ ishydrogen or methyl, and the sum of x and y is an average number fromabout 5 to about 15.

Specific examples of surfactants and surfactant combinations for use inthe surfactant component of the concentrate formulations include TOMADOL1-7 in combination with a dialkoxylated quaternary ammonium saltsurfactant such as ETHOQUAD C12 70PG, a PEG 2 coco methyl ammoniumchloride from Akzo Nobel (Chicago, Ill.), PEG 5 coco methyl ammoniumchloride, PEG 5 tallow methyl ammonium chloride, PEG 5 ditallow ammoniumbromide, or PEG 10 ditallow ammonium bromide. In addition, it may beuseful to include glycerin, propylene glycol or other glycols whenformulating concentrates.

In order to provide a suitably stable concentrate solution, theconcentration of the surfactant component is typically at least about5%, preferably from about 5% to about 50% by weight. The surfactantcomponent and its concentration are preferably selected so as to obtaina “storage stable” concentrate composition. By “storage-stable,” it ismeant not exhibiting phase separation on exposure to temperatures up toabout 50° C., and preferably not forming crystals of glyphosate or saltor other ingredients thereof on exposure to a temperature of about 0° C.for a period of up to about 7 days (i.e., the concentrate compositionhas a crystallization point of 0° C. or lower). For aqueous solutionconcentrates, high temperature storage stability is often indicated by acloud point of about 50° C. or more. Cloud point of a composition isnormally determined by heating the composition until the solutionbecomes cloudy, and then allowing the composition to cool, withagitation, while its temperature is continuously monitored. Atemperature reading taken when the solution clears is a measure of cloudpoint. A cloud point of 50° C. or more is normally considered acceptablefor most commercial purposes for a glyphosate concentrate formulation.Ideally the cloud point should be 60° C. or more, and the compositionshould withstand temperatures as low as about −10° C., preferably as lowas about −20° C., more preferably as low as about −30° C., for up toabout 7 days without phase separation (i.e., without separation offrozen water or solid insoluble surfactant from the composition) andwithout crystal growth (even in the presence of seed crystals of theglyphosate salt).

So long as measures are taken to ensure adequate solubility, theconcentrates may generally contain at least about 2%, for example fromabout 2% to about 25% by weight (a.e.) of the fatty acid component andoptionally at least about 3%, for example from about 3% to about 18% byweight of an inorganic ammonium salt such as ammonium sulfate. However,in order to maintain sufficient solubility, it may be necessary toadjust the proportions of the fatty acid component and ammonium sulfateas compared to the above-described RTU formulations. In suchembodiments, the concentration of the fatty acid component may be nomore than about 10% by weight (a.e.), preferably from about 1% to about5% by weight (a.e.), and the concentration of ammonium sulfate or otherinorganic ammonium salt may be no more than about 15% by weight,preferably from about 2% to about 5% by weight. If necessary to attainthe desired herbicidal efficacy and early symptomology, theconcentration of the fatty acid component and/or inorganic ammonium saltmay be increased in the formulation to be applied eithercontemporaneously with or after dilution of the concentrate.Furthermore, it may be advantageous to entirely omit the optionalinorganic ammonium salt from the concentrate composition and, if desiredin the formulation to be applied, to add ammonium sulfate or otherammonium salt at the time of dilution of the concentrate.

One example of a concentrate in accordance with the present inventioncontains about 13 by weight (a.e.) of the glyphosate component as theisopropylammonium salt of N-(phosphonomethyl)glycine, about 3% by weight(a.e.) of pelargonic acid as the fatty acid component about 14% byweight of ETHOQUAD C12 70PG and about 23% by weight of TOMADOL 1-7 asthe surfactant component and the remainder water.

The concentrate compositions of the present invention are diluted with asuitable amount of water and optionally augmented as necessary toprovide a tank mix having a composition substantially conforming to theRTU compositions of the present invention and ready for sprayapplication to the foliage of unwanted plants.

The present invention is also directed to a method for killing orcontrolling weeds or other unwanted plants by spraying or otherwiseapplying a herbicidally effective amount of the RTU or dilutedconcentrate formulations described herein to the foliage of the plantsto be treated. The herbicidal spray compositions included in the presentinvention can be applied to the foliage of the plants to be treatedthrough any of the appropriate methods that are well known to thosehaving skill in the art. In one embodiment, the RTU composition ispackaged in a portable container suitable for hand carry by the user andfitted with an apparatus for manually releasing the composition from thecontainer onto the foliage of the plants to be treated in the form of aspray.

The compositions of the present invention can be used to kill or controlthe growth of a wide variety of plants. Particularly important annualdicotyledonous plant species include, without limitation, velvetleaf(Abutilon theophrasti), pigweed (Amaranthus spp.), buttonweed (Borreriaspp.), oilseed rape, canola, indian mustard, etc. (Brassica spp.),commelina (Commelina spp.), filaree (Erodium spp.), sunflower(Helianthus spp.), morningglory (Ipomoea spp.), kochia (Kochiascoparia), mallow (Malva spp.), wild buckwheat, smartweed, etc.(Polygonum spp.), purslane (Portulaca spp.), Russian thistle (Salsolaspp.), sida (Sida spp.), wild mustard (Sinapis arvensis) and cocklebur(Xanthium spp.).

Particularly important annual monocotyledonous plant species that may bekilled or controlled using the compositions of the present inventioninclude, without limitation, wild oat (Avena fatua), carpetgrass(Axonopus spp.), downy brome (Bromus tectorum), crabgrass (Digitariaspp.), barnyardgrass (Echinochloa crus-galli), goosegrass (Eleusineindica), annual ryegrass (Lolium multiflorum), rice (Oryza sativa),ottochloa (Ottochloa nodosa), bahiagrass (Paspalum notatum), canarygrass(Phalaris spp.), foxtail (Setaria spp.), wheat (Triticum aestivum) andcorn (Zea mays).

Particularly important perennial dicotyledonous plant species forcontrol of which a composition of the invention can be used include,without limitation, mugwort (Artemisia spp.), milkweed (Asclepias spp.),Canada thistle (Cirsium arvense), field bindweed (Convolvulus arvensis)and kudzu (Pueraria spp.).

Particularly important perennial monocotyledonous plant species forcontrol of which a composition of the invention can be used include,without limitation, brachiaria (Brachiaria spp.), bermudagrass (Cynodondactylon), quackgrass (Elymus repens), lalang (Imperata cylindrica),perennial ryegrass (Lolium perenne), guineagrass (Panicum maximum),dallisgrass (Paspalum dilatatum), reed (Phragmites spp.), johnsongrass(Sorghum halepense) and cattail (Typha spp.).

Other particularly important perennial plant species for control ofwhich a composition of the invention can be used include, withoutlimitation, horsetail (Equisetum spp.), bracken (Pteridium aquilinum),blackberry (Rubes spp.) and gorse (Ulex europaeus).

Suitable herbicidally efficacious application or spray rates used in thepractice of the present invention will vary depending on the particularcomposition and concentration of active ingredients, the desiredeffects, plant species treated, weather and other factors. Whatconstitutes a “desired effect” varies according to the standards andpractice of those who investigate, develop, market and use compositionsand the selection of application rates that are herbicidally effectivefor a composition of the invention is within the skill of those skilledin the art.

The herbicidal composition of the present invention is preferablyapplied to plants at a rate sufficient to give both long term control ofplant growth and early visual symptoms of treatment. Typically, thecomposition is applied at rate sufficient to provide at least about 35%,preferably at least about 50%, more preferably at least about 80% andeven more preferably at least about 85% control of a treated plantspecies as measured by growth reduction or mortality 1 day aftertreatment, while producing visually apparent phytotoxic effects no laterthan about 24 hours, preferably no later than about 12 hours and morepreferably no later than about 3 hours after treatment. Applicationrates are classified as a “spray-to-wet” usually expressed as amount ofcomposition per unit area treated (e.g., as gallons/acre or liters/m²).In the practice of the present invention, suitable long term control andearlier symptomology are generally achieved by applying the RTUcomposition at a spray rate of about 145 gallons/acre (0.136 liter/m²).

DEFINITIONS

The term “hydrocarbyl” as used herein describes organic compounds orradicals consisting exclusively of the elements carbon and hydrogen.These moieties include alkyl, alkenyl, alkynyl, and aryl moieties. Thesemoieties also include alkyl, alkenyl, alkynyl, and aryl moietiessubstituted with other aliphatic or cyclic hydrocarbon groups, such asalkaryl, alkenaryl and alkynaryl. Unless otherwise indicated, thesemoieties preferably comprise 1 to 30 carbon atoms.

The term “substituted hydrocarbyl” as used herein describes hydrocarbylmoieties that are substituted with at least one atom other than carbon,including moieties in which a carbon chain atom is substituted with ahetero atom such as nitrogen, oxygen, silicon, phosphorous, boron,sulfur, or a halogen atom. These substituents include halogen,heterocyclo, alkoxy, alkenoxy, alkynoxy, aryloxy, hydroxy, protectedhydroxy, ketal, acyl, acyloxy, nitro, amino, amido, cyano, thiol,acetal, sulfoxide, ester, thioester, ether, thioether, hydroxyalkyl,urea, guanidine, amidine, phosphate, amine oxide, and quaternaryammonium salt.

The term “aryl” as used herein alone or as part of another group denoteoptionally substituted homocyclic aromatic groups, preferably monocyclicor bicyclic groups containing from 6 to 12 carbons in the ring portion,such as phenyl, biphenyl, naphthyl, substituted phenyl, substitutedbiphenyl or substituted naphthyl. Phenyl and substituted phenyl are themore preferred aryl.

The term “aralkyl” as used herein denotes a group containing both alkyland aryl structures such as benzyl.

Unless otherwise indicated, the term “hydroxyalkyl” includes alkylgroups substituted with at least one hydroxy group, e.g.,bis(hydroxyalkyl)alkyl, tris(hydroxyalkyl)alkyl andpoly(hydroxyalkyl)alkyl groups. Preferred hydroxyalkyl groups includehydroxymethyl (—CH₂OH), and hydroxyethyl (—C₂H₄OH),bis(hydroxy-methyl)methyl (—CH(CH₂OH)₂), and tris(hydroxymethyl)methyl(—C(CH₂OH)₃).

The term “cyclic” as used herein alone or as part of another groupdenotes a group having at least one closed ring, and includes alicyclic,aromatic (arene) and heterocyclic groups.

When a maximum or minimum “average number” is recited herein withreference to a structural feature such as oxyethylene units, it will beunderstood by those skilled in the art that the integer number of suchunits in individual molecules in a surfactant preparation typicallyvaries over a range that can include integer numbers greater than themaximum or smaller than the minimum “average number”. The presence in acomposition of individual surfactant molecules having an integer numberof such units outside the stated range in “average number” does notremove the composition from the scope of the present invention, so longas the “average number” is within the stated range and otherrequirements are met.

Herbicidal effectiveness is one of the biological effects that can beenhanced through this invention. “Herbicidal effectiveness,” as usedherein, refers to any observable measure of control of plant growth,which can include one or more of the actions of (1) killing, (2)inhibiting growth, reproduction or proliferation, and (3) removing,destroying, or otherwise diminishing the occurrence and activity ofplants. The herbicidal effectiveness data set forth herein report“control” as a percentage following a standard procedure in the artwhich reflects a visual assessment of plant mortality and growthreduction by comparison with untreated plants, made by techniciansspecially trained to make and record such observations. In all cases, asingle technician makes all assessments of percent control within anyone experiment or trial.

The following Examples are presented to illustrate the present inventionas well as some of the various embodiments of the invention. Theinvention is not intended to be limited to any of the details in theseExamples.

EXAMPLES

The examples will permit better understanding of the invention and itsadvantages and certain variations of execution. An experimental designwas performed to investigate the effect and interactions of componentsin RTU glyphosate formulations that give fast symptom development onweeds. A series of glyphosate formulations were prepared with variedconcentrations of glyphosate salt (e.g., 2% isopropylammonium (IPA) saltof glyphosate (1.48% a.e.)), pelargonic acid, surfactant(s) andinorganic ammonium salt (e.g., ammonium sulfate). The test was to aid inthe selection of optimum levels of each component in the formulation andto investigate any interaction between the ingredients.

1. Formulations

In order to assess fast symptomology and long term efficacy, commerciallawn and garden products were compared with experimental aqueousherbicide formulations generated from glyphosate salt (e.g.,isopropylammonium salt, GLYPH), pelargonic acid (PA), inorganic ammoniumsalt (e.g., ammonium sulfate, AMS) and various surfactants (SURF) andadditives (OTH) as indicated in Tables 1.1, 1.2, and 1.3. Theformulations were tested on a broad spectrum of lawn and garden weedsdiscussed hereinafter.

TABLE 1.1 Tested Standard Formulations GLYPH wt % PA AMS OTHER SURF. 1SURF. 2 CODE ae wt % wt % OTHER wt % SURF. 1 wt % SURF. 2 wt % STD 154.2 OTH9 2.9 STD 2 1.4 STD 3 1.48 STD 4 OTH12 22.9 STD 5 OTH9 0.18OTH11 0.06 STD 6 13.3 OTH9 0.73 STD 7 37.2 141F1T 13.3 OTH9 0.5 SUX9T 9SUN2X 7 599F5T 1.48 0 0 OTH9 0.055 SUX9T 1 SUN2X 0.078 (K⁺) 305G4T 1.480 0 OTH12 1.5 SUB1 7.6 OTH1 5 OTH2 0.1 OTH3 0.01 306H2T 1.48 0 0 OTH120.75 SUB1 4.2 OTH1 3.4 OTH2 0.1 OTH3 0.01 307L6T 1.48 0 0 OTH12 0.5 SUB11.2 SUN6A 3.6 OTH1 1.2 OTH2 0.03 UNTRT 0 0 0

TABLE 1.2 Tested Experimental Formulations GLYPH Stability IPA wt PASURF SURF (cloud pt., (% wt AMS OTHER SURF #1 SURF #2 crystal. Codea.e.) (%) wt % OTHER wt % #1 wt % #2 wt % Pt) 295L1V 1.48 2 OTH3 0.01SUB1 0.5 Stable OTH4 2.1 OTH5 0.1 451A2K 1.48 2 2 OTH3 0.01 SUB1 0.5Stable OTH4 2.1 OTH5 0.1 453C7P 1.48 2 2 OTH3 0.01 SUB1 0.5 SUN6A 1.5Stable OTH4 2.1 OTH5 0.1 489H1P 0.74 2 2 OTH2 0.1 SUB1 0.3 Stable OTH30.01 OTH4 2.1 OTH13 0.016 490K9E 0.74 2 2 OTH3 0.01 SUN6A 1.5 StableOTH4 2.1 OTH5 0.1 OTH13 0.016 998F3S 1.48 2 OTH2 0.03 SUB1 0.5 StableOTH4 2.1 578W5Y 1.42 2 OTH2 0.03 SUB1 0.5 Stable 440A2X 1.48 OTH2 0.03SUN6B 3.6 Layers 440B3Z 1.48 OTH2 0.03 SUN6C 3.6 Layers 440C4S 1.48 OTH20.03 SUN6A 3.6 Stable 440D6H 1.48 OTH2 0.03 SUN6D 3.6 Stable 440E7R 1.48OTH2 0.03 SUN7A 3.6 Stable 440F8P 1.48 OTH2 0.03 SUN7X 3.6 Stable 440G3T1.48 OTH2 0.03 SUN7J 3.6 Stable 440H5C 1.48 OTH2 0.03 SUN1A 3.6 Stable440I2E 1.48 OTH2 0.03 SUN8T 3.6 Stable 440J9Q 1.48 OTH2 0.03 SUN8N 3.6Stable 440K1L 1.48 OTH2 0.03 SUN8M 3.6 Stable 440L5W 1.48 OTH2 0.03SUN8A 3.6 Stable 440M8D 1.48 OTH2 0.03 SUN8S 3.6 Stable 440N6G 1.48 OTH20.03 SUN3X 3.6 Stable 440O2N 1.48 OTH2 0.03 SUN3Z 3.6 Stable 440P4V 1.48OTH2 0.03 SUN4Y 3.6 Stable 440Q7S 1.48 OTH2 0.03 SUN4G 3.6 Stable 440R3F1.48 OTH2 0.03 SUN2V 3.6 Stable 441A9S 1.48 2 OTH2 0.03 SUN6B 3.6 LayersOTH4 2.1 441B4W 1.48 2 OTH2 0.03 SUN6C 3.6 Layers OTH4 2.1 441C2X 1.48 2OTH2 0.03 SUN6A 3.6 Stable OTH4 2.1 441D5C 1.48 2 OTH2 0.03 SUN6D 3.6Stable OTH4 2.1 441E8S 1.48 2 OTH2 0.03 SUN7A 3.6 Stable OTH4 2.1 441F6N1.48 2 OTH2 0.03 SUN7X 3.6 Stable OTH4 2.1 441G1R 1.48 2 OTH2 0.03 SUN7J3.6 Stable OTH4 2.1 441H7T 1.48 2 OTH2 0.03 SUN1A 3.6 Stable OTH4 2.1441I2J 1.48 2 OTH2 0.03 SUN8T 3.6 Stable OTH4 2.1 441J3S 1.48 2 OTH20.03 SUN8N 3.6 Stable OTH4 2.1 441K7H 1.48 2 OTH2 0.03 SUN8M 3.6 StableOTH4 2.1 441L2W 1.48 2 OTH2 0.03 SUN8A 3.6 Stable OTH4 2.1 441M3D 1.48 2OTH2 0.03 SUN8S 3.6 Stable OTH4 2.1 441N9H 1.48 2 OTH2 0.03 SUN3X 3.6Stable OTH4 2.1 441O6S 1.48 2 OTH2 0.03 SUN3Z 3.6 Stable OTH4 2.1 441P4J1.48 2 OTH2 0.03 SUN4Y 3.6 Stable OTH4 2.1 441Q5S 1.48 2 OTH2 0.03 SUN4G3.6 Stable OTH4 2.1 441R3P 1.48 2 OTH2 0.03 SUN2V 3.6 Stable OTH4 2.1433S5C 1.48 2 OTH2 0.1 SUN6A 2.5 SUB1 0.5 Stable OTH4 2.1 469A1T 1.48 21 OTH2 0.1 SUN6A 2.5 SUB1 0.5 Stable OTH4 2.1 469B8T 1.48 1 2 OTH2 0.1SUN6A 3.5 Stable OTH4 1.1 480C5X 1.48 2 1 OTH2 0.1 SUN6A 2.5 Stable OTH42.1 483D2T 1.48 2 2 OTH2 0.1 SUN6A 3.5 SUB1 0.5 Stable OTH4 2.1 495G6A1.48 2 OTH2 0.1 SUN6A 2.5 Stable 475B6Y 1.48 2 2 OTH2 0.1 SUN6A 1.5Stable OTH4 2.1 476K3W 1.48 1 2 OTH2 0.1 SUN6A 1.5 Stable OTH4 1.1513U9D 1.48 1 OTH2 0.1 SUN6A 3.5 Stable 471C9T 1.48 2 1 OTH2 0.1 SUN6A3.5 SUB1 0.5 Stable OTH4 2.1 471D3T 1.48 OTH2 0.1 SUN6A 1.5 SUB1 0.5Stable 474E7T 1.48 OTH2 0.1 SUN6A 3.5 SUB1 0.5 Stable 420S8C 1.48 1 OTH20.1 SUN6A 2.5 SUB1 0.5 Stable 435W6E 1.48 1 2 OTH2 0.1 SUN6A 1.5 SUB10.5 Stable OTH4 1.1 421L5N 1.48 2 OTH2 0.1 SUN6A 3.5 Stable 525R9B 1.481 OTH2 0.1 SUN6A 1.5 SUB1 0.5 Stable OTH4 1.1 515N3B 1.48 2 1 OTH2 0.1SUN6A 1.5 SUB1 0.5 Stable OTH4 2.1 520C4X 1.48 2 OTH2 0.1 SUN6A 3.5Stable OTH4 2.1 520W9S 1.48 1 1 OTH2 0.1 SUN6A 3.5 SUB1 0.5 Stable OTH41.1 345R6C 1.48 OTH2 0.1 SUN6A 2.5 Stable 350F1L 1.48 1 2 OTH2 0.1 SUN6A2.5 SUB1 0.5 Stable OTH4 1.1 235W9D 1.48 2 OTH2 0.1 SUN6A 1.5 StableOTH4 2.1 240S8G 1.48 2 2 OTH2 0.1 SUN6A 2.5 Stable OTH4 2.1 240D3F 1.482 1 OTH2 0.1 SUN6A 2.5 Stable OTH4 2.1 675W3T 1.48 1 2 OTH2 0.1 SUN6A1.5 Stable OTH4 1.1 245M9S 1.48 2 OTH4 2.1 SUN6A 2.5 Stable 737F2S 0.721 AMN OTH2 0.03 SUB2 0.15 Stable 2.4 OTH3 0.01 OTH4 1.1 490W1M 1.45 2 2OTH1 0.66 SUN6A 3.6 Stable OTH2 0.03 OTH4 2.1 735T2H 1.45 2 2 OTH1 0.66SUN6A 3.6 SUB1 0.5 Stable OTH2 0.03 OTH4 1 740M5C 1.45 1 2 OTH1 0.66SUB1 0.5 Stable OTH2 0.03 OTH4 1 750R8X 1.45 2 OTH1 0.66 SUN9X 3.6Stable OTH2 0.03 OTH4 2.1 920M2V 1.45 2 2 OTH1 0.66 SUN9X 3.6 SUB1 0.5Stable OTH2 0.03 OTH4 2.1 308J8T 1.48 OTH1 5 SUB1 7.6 Stable OTH2 0.1322K9T 1.45 2 OTH1 0.66 SUN6A 3.6 Stable OTH2 0.03 OTH6 0.01 022K8T 1.482 2 OTH2 0.1 SUB1 0.5 SUN6A 2.5 Stable OTH4 1 452B9X 1.48 1 2 OTH2 0.1SUN6A 2.5 Stable OTH3 0.01 OTH4 2 454D4K 1.48 2 1 OTH2 0.1 SUN6A 2.5Stable OTH3 0.01 OTH4 2.6 455E8S 1.48 2 OTH2 0.1 SUN6A 3.5 Stable OTH30.01 OTH4 2.6 456F6H 1.48 1 OTH2 0.1 SUN6A 3.5 Stable OTH3 0.01 OTH4 2457G1T 1.48 2 0.75 OTH2 0.1 SUN6A 2 Stable OTH3 0.05 OTH4 0.5 458W3S1.48 2 2 OTH2 0.1 SUB1 0.5 SUN6A 3.5 Stable OTH3 0.05 OTH4 2

TABLE 1.3 Standards, Surfactants, and other Additives STANDARDS CODELABEL STD 1 ROUNDUP QUICK PRO STD 2 ROUNDUP FAST-ACT FOAM STD 3STATESMAN RTU STD 4 BARRIER H STD 5 SPECTRACIDE RTU STD 6 ROUNDUP CONCPLUS STD 7 ROUNDUP SUPER CONC CODE LABEL COMPONENTS SURFACTANTS SUB1112D5Y Surfactant blend; Tallowamine ethoxylate (~10 EO) andalkylethoxylate phosphate ester formulations. SUB2 117P3W Etheraminesurfactant (isotridecyloxypropylamine EO5). SUB3 818I7M Surfactant blendof Tallowamine ethoxylate (15EO)] in Polyethylene glycol & Ethyleneglycol SUC1A AGRISOL A- Blend of 2EO Methylcocoammonium quat, 250HC 10EOisotridecyl alcohol in Dipropylene glycol (DPG) SUN1A TRITON X-1009-10EO Octylphenol SUN2V WICONOL TD- 20EO Tallowamine 1407 SUN3X MAKON 66EO Nonylphenol SUN3Z MAKON 12 12EO Nonylphenol SUN4G DD-5 5EODodecylphenol SUN4Y DD-10 10EO Dodecylphenol SUN5H C-6101 50% 10.5EOTallowamine in 50% Dipropylene glycol (DPG) SUN6C TOMADOL 1-3 Linearalcohol ethoxylate 3EO Undecyl alcohol SUN6B TOMADOL 1-5 Linear alcoholethoxylate 5EO Undecyl alcohol SUN6A TOMADOL 1-7 Linear alcoholethoxylate 7EO Undecyl alcohol SUN6D TOMADOL 1-9 Linear alcoholethoxylate 9EO Undecyl alcohol SUN7A TOMADOL 25-3 Linear C12-15 alcoholwith ~3 moles (average) EO ethylene oxide. SUN7X TOMADOL 25-7 LinearC12-15 alcohol with 7 moles (average) EO SUN7J TOMADOL 25-9 LinearC12-15 alcohol with 9 moles (average) EO SUN8A SURFONIC Low foamingC11-12 linear alcohol L12-7 alkoxylate (EO/PO); degree of alkoxylation =7 SUN8M SURFONIC Low foaming C12-14 linear alcohol L24-6.5 alkoxylate(EO/PO); degree of alkoxylation = 6.5 SUN8S SURFONIC Low foaming C12-14linear alcohol L24-7 alkoxylate (EO/PO); degree of alkoxylation = 7SUN8N SURFONIC Low foaming C12-14 linear alcohol L24-9 alkoxylate(EO/PO); degree of alkoxylation = 9 SUN8T SURFONIC Low foaming C12-14linear alcohol L24-12 alkoxylate (EO/PO); degree of alkoxylation = 12SUN9X TERGITOL 15- C11-C15 linear secondary alcohol S-9 ethoxylate; 9 EOSUX9T SILWET 800 Organosilicone surfactant SUN2X TRIMETHYL COCOAMINEOTHER ADDITIVES OTH1 PROPYLENE Solvent; antifreeze GLYCOL OTH2 PROXELGXL Preservative OTH3 SAG 10 Antifoam OTH4 KOH Base OTH5 NIPACIDEPreservative BIT20DPG OTH6 SHIN ETSU Antifoam KM90 OTH7 LEGEND MKPreservative OTH8 AMMONIUM Salt NITRATE OTH9 DIQUAT Herbicide DIBROMIDEOTH10 GLUFOSINATE Herbicide AMMONIUM OTH11 FLUAZIFOP-p- Herbicide BUTYLOTH12 CITRONELLOL OTH13 IMAZAPIC Herbicide

2. Stability Test and Results

Various formulations were maintained at constant temperature for a fixedperiod and monitored for changes in color, homogeneity and appearanceafter thawing. The formulations were also cycled through temperatureextremes (i.e., at low temperatures of −20° C. and −5° C. for the fixedperiod then raised to the higher temperatures of 20° C. and 5° C.,respectively) and changes monitored. Results are presented in Table 1.2above.

3. Greenhouse Test and Results

Standard post emergence herbicide application procedures were used, asdescribed below, to formulations listed in Tables 1.1-1.3.

Seeds of the plant species, white clover (TRFRE), tall fescue (FESAR),large crabgrass (DIGSA) and common purslane (POROL), were planted in 3.5in square pots in a soil mix which was previously steam sterilized andprefertilized with a 14-28-14 N—P—K slow release fertilizer at aconcentration of 3.53 g/L. The pots were placed in a greenhouse withsub-irrigation. About one week after emergence, seedlings were thinnedas needed, including removal of any unhealthy or abnormal plants, tocreate a uniform series of test pots.

The plants were maintained for the duration of the test in thegreenhouse where they received a minimum of 14 hours of light per day.If natural light was insufficient to achieve the daily requirement,artificial light with an intensity of approximately 475 microeinsteinswas used to make up the difference. Exposure temperatures averaged about27° C. during the day and about 21° C. during the night. Plants weresub-irrigated throughout the test to ensure adequate soil moisturelevels.

Pots were assigned to different treatments in a randomized experimentaldesign with 3 replications. A set of pots was left untreated as areference against which effects of the treatments could later beevaluated. Application of tested formulations was made by spraying witha lawn and garden 24-oz trigger sprayer fitted with an RTU pumpapplicator calibrated to deliver a spray volume of 1348 liters perhectare (l/ha). After treatment, pots were returned to the greenhouseuntil ready for evaluation. Treatments were made using dilute aqueouscompositions.

For evaluation of herbicidal effectiveness, all plants in the test wereexamined by a single practiced technician, who recorded percent control,a visual measurement of the effectiveness of each treatment bycomparison with untreated plants. Control of 0% indicates no effect, andcontrol of 100% indicates that all of the plants are completely dead.Control of 85% or more is in most cases considered acceptable for normalherbicide use; however in greenhouse tests such as those for theexamples it is normal to apply compositions at rates which give lessthan 85% control, as this makes it easier to discriminate amongcompositions having different levels of effectiveness. The reported %control values represent the average for all replicates of eachtreatment.

The results of the Greenhouse Tests are summarized in Tables 3a-3c. Thedata is reported as % control (treated vs. untreated) at 1, 3, 5, 7, 14and 21 DAT (days after treatment) for each species in Table 3a.Similarly the data is reported at 1, 3, 7, 14 and 21 DAT in Tables 3band 3c.

TABLE 3a Results of Greenhouse Efficacy Study of Experimental andStandard Glyphosate Formulations on Lawn & Garden Weed Spectrum TRFREFESAR DIGSA SPECIES AVE. 1, 3, 5, 7, 1, 3, 5, 7, 1, 3, 5, 7, 1, 3, 5, 7,CODE 14, 21 DAT 14, 21 DAT 14, 21 DAT 14, 21 DAT 307F1S 53, 83, 88, 25,68, 79, 55, 58, 72, 44, 70, 80, 90, 87, 83 80, 85, 98 67, 72, 87 79, 81,89 STD 1 60, 89, 94, 47, 85, 91, 65, 80, 88, 57, 85, 91, 97, 96, 93 93,93, 99 93, 96, 95 94, 95, 95 STD 2 68, 68, 67, 70, 89, 98, 67, 78, 80,68, 79, 82, 67, 64, 75 97, 98, 99 82, 87, 99 82, 83, 91 STD 3 78, 81,90, 27, 73, 83, 72, 77, 79, 59, 77, 84, 89, 87, 95 88, 95, 100 76, 80,88 85, 87, 94 737F2S 72, 72, 77, 47, 68, 74, 53, 65, 77, 57, 68, 76, 78,73, 70 74, 85, 99 82, 87, 92 78, 81, 87 998F3S 76, 77, 82, 67, 87, 91,48, 63, 75, 64, 76, 83, 83, 80, 92 89, 93, 98 76, 92, 98 83, 88, 96141F1T 52, 87, 86, 25, 77, 83, 50, 72, 82, 43, 79, 84, 91, 91, 87 92,96, 100 85, 96, 93 89, 94, 93 STD 4 85, 84, 84, 80, 78, 73, 78, 82, 72,81, 81, 76, 79, 65, 25 69, 62, 27 62, 52, 27 70, 59, 26 469A1T 84, 87,96, 83, 89, 93, 60, 70, 77, 76, 82, 88, 94, 92, 93 89, 89, 98 81, 90, 9788, 90, 96 469B8T 73, 78, 84, 79, 94, 98, 75, 84, 88, 76, 85, 90, 82,82, 85 97, 99, 100 93, 97, 100 91, 93, 95 471C9T 78, 83, 91, 58, 83, 90,68, 80, 83, 68, 82, 88, 90, 89, 95 91, 93, 99 82, 91, 100 88, 91, 98471D3T 83, 87, 88, 70, 84, 92, 60, 81, 85, 71, 84, 88, 88, 86, 83 92,97, 97 88, 88, 98 89, 90, 93 474E7T 83, 86, 86, 57, 76, 82, 62, 77, 80,67, 80, 83, 89, 89, 90 84, 84, 92 84, 93, 100 86, 89, 94 599F5T 68, 92,99, 22, 78, 95, 50, 73, 81, 47, 81, 92, 99, 99, 99 95, 95, 98 85, 89, 8593, 94, 94 305G4T 62, 80, 87, 10, 42, 63, 30, 47, 70, 34, 56, 73, 87,85, 90 83, 93, 99 78, 93, 100 83, 90, 96 306H2T 53, 76, 86, 4, 15, 45,25, 47, 73, 27, 46, 68, 87, 89, 94 75, 93, 99 87, 100, 100 83, 94, 98307L6T 70, 78, 87, 23, 72, 78, 60, 70, 82, 51, 73, 83, 86, 84, 83 83,87, 100 83, 95, 99 84, 89, 94 308J8T 48, 77, 87, 7, 12, 40, 15, 30, 55,23, 40, 61, 91, 99, 99 63, 83, 99 80, 100, 100 78, 94, 100 322K9T 88,93, 99, 12, 50, 65, 58, 70, 70, 53, 71, 78, 99, 100, 99 78, 88, 99 73,82, 98 84, 90, 99

Discussion:

This test demonstrates that the formulation with 1% PA and 2.4% ammoniumnitrate (737F2S) does not perform as well as to fast symptomdevelopment, particularly on tall fescue, as the formulations thatcontain 2% PA or 1% PA and 2% AMS.

The data also shows that ammonium sulfate does not increase the fastsymptom development on grass species (crab and tall fescue) when theformulation only contains the NIS surfactant (STD 3 vs. 322K₉T). Thedata also shows that an iso-alcohol surfactant gives equivalent fastsymptom development when compared to a completely linear alcohol whencombined with PA+/−AMS (comparing 305G4T & 306H2T to 474E7T). Also inthis trial, 308J8T which contains 7.6% of the proprietary blend(alkylphosphate ester plus tallowamine ethoxylate surfactant) does notshow equivalent fast symptom development to the PA+/−NIS+/−AMSformulations.

TABLE 3b Results of Greenhouse Efficacy Study of Experimental GlyphosateFormulations containing various Nonionic Surfactants with or withoutPelargonic Acid on Lawn & Garden Weed Spectrum DIGSA POROL FESAR TRFRE1, 3, 7, 14, 1, 3, 7, 14, 1, 3, 7, 14, 1, 3, 7, 14, CODE 21 DAT 21 DAT21 DAT 21 DAT 440A2X 72, 82, 96, 70, 82, 92, 65, 80, 89, 85, 93, 93, 99,100 91, 93 89, 92 92, 90 440B3Z 73, 81, 94, 73, 87, 94, 40, 65, 78, 83,92, 93, 98, 100 94, 98 85, 84 89, 86 440C4S 75, 78, 91, 73, 85, 95, 50,58, 77, 82, 88, 93, 93, 99 97, 99 86, 96 93, 91 440D6H 62, 65, 72, 64,77, 84, 20, 33, 47, 70, 80, 90, 90, 100 82, 82 72, 90 86, 84 440E7R 67,83, 87, 55, 67, 81, 18, 35, 58, 75, 77, 97, 97, 99 87, 93 73, 95 98, 99440F8P 60, 75, 92, 45, 60, 83, 7, 37, 48, 65, 70, 90, 97, 100 85, 98 72,96 91, 94 440G3T 58, 68, 73, 40, 63, 85, 4, 22, 38, 60, 70, 96, 87, 10090, 98 65, 100 98, 100 440H5C 40, 55, 68, 25, 43, 82, 5, 20, 33, 70, 75,97, 99, 100 97, 100 72, 100 98, 100 440I2E 55, 62, 67, 42, 70, 84, 5,15, 30, 65, 65, 82, 85, 100 89, 99 67, 90 85, 85 440J9Q 67, 68, 73, 53,76, 88, 12, 30, 53, 68, 73, 88, 88, 100 88, 97 71, 93 92, 92 440K1L 63,82, 90, 60, 75, 83, 20, 47, 53, 73, 73, 82, 93, 100 88, 96 73, 86 90, 90440L5W 75, 87, 96, 75, 86, 93, 43, 67, 72, 82, 87, 89, 94, 100 94, 9778, 91 95, 95 440M8D 68, 82, 93, 63, 77, 84, 15, 33, 40, 73, 75, 93, 95,100 91, 99 72, 100 99, 99 440N6G 45, 65, 75, 33, 42, 75, 5, 13, 25, 62,68, 90, 100, 100 93, 100 75, 100 97, 99 440O2N 47, 73, 78, 30, 57, 82,10, 25, 48, 65, 70, 83, 96, 100 94, 99 77, 100 95, 98 440P4V 22, 45, 62,5, 20, 69, 5, 10, 22, 50, 60, 83, 100, 100 100, 100 75, 100 98, 99440Q7S 20, 45, 65, 10, 27, 67, 3, 5, 17, 65, 38, 56, 91, 98, 100 95, 100100 100, 100 440R3F 45, 55, 68, 17, 53, 80, 4, 15, 23, 45, 55, 82, 88,100 98, 100 63, 100 93, 99 441A9S 82, 93, 99, 90, 96, 100, 78, 87, 94,93, 96, 98, 99, 99 100, 100 94, 95 99, 100 441B4W 80, 85, 96, 86, 92,100, 78, 87, 93, 92, 98, 98, 96, 97 100, 100 94, 94 99, 99 441C2X 82,92, 98, 80, 90, 99, 67, 84, 90, 96, 99, 100, 99, 100 99, 100 95, 100100, 100 441D5C 78, 85, 89, 82, 92, 98, 63, 77, 82, 87, 88, 89, 94, 9699, 100 87, 95 92, 92 441E8S 77, 92, 101, 90, 94, 99, 63, 70, 74, 83,88, 91, 100, 100 100, 100 83, 94 94, 94 441F6N 75, 87, 96, 88, 95, 97,57, 67, 80, 82, 93, 94, 98, 99 99, 99 84, 99 94, 94 441G1R 72, 83, 94,74, 88, 93, 50, 67, 72, 77, 80, 83, 94, 99 96, 100 82, 97 86, 93 441H7T70, 80, 95, 52, 67, 88, 65, 77, 88, 75, 80, 87, 95, 100 99, 100 92, 9988, 96 441I2J 70, 80, 94, 78, 90, 95, 48, 63, 82, 80, 88, 93, 96, 10097, 100 90, 98 95, 99 441J3S 68, 82, 91, 85, 93, 98, 63, 73, 88, 78, 83,85, 96, 100 99, 100 95, 99 83, 88 441K7H 70, 82, 95, 75, 87, 97, 57, 78,82, 84, 88, 94, 96, 100 98, 100 92, 99 99, 100 441L2W 70, 89, 100, 80,92, 99, 53, 75, 83, 75, 85, 82, 100, 100 100, 100 92, 94 86, 88 441M3D70, 87, 96, 90, 96, 100, 60, 82, 83, 78, 87, 90, 98, 100 100, 100 90, 9991, 91 441N9H 70, 82, 95, 63, 74, 84, 60, 79, 87, 60, 67, 70, 96, 10092, 99 95, 98 80, 88 441O6S 60, 81, 91, 32, 60, 91, 40, 62, 75, 63, 69,89, 97, 100 99, 100 95, 99 99, 99 441P4J 60, 82, 88, 38, 65, 82, 32, 58,68, 63, 70, 78, 99, 100 94, 99 83, 94 87, 87 441Q5S 62, 78, 83, 67, 78,90, 33, 63, 70, 75, 80, 88, 96, 99 98, 99 80, 98 94, 94 441R3P 72, 83,88, 70, 78, 94, 62, 70, 72, 78, 83, 86, 93, 98 97, 90 75, 91 89, 89

Discussion:

This test explored the type of nonionic surfactant that would give fastsymptom development when applied either with glyphosate alone or incombination with PA.

Note, the formulations that contained the linear (TOMADOL, SURFONIC L)surfactants gave much better 1 DAT symptoms than the alkylphenol typesurfactants (TRITON X-100, MAKON 6 or 12, DD 10 or 5) or the highlybranched surfactant WITCONOL TD1407 (2,4,6,8 tetramethylnonyl alcoholethoxylate, EO7). Also demonstrated was the combination of these mostlylinear surfactants with pelargonic acid gave in general better fastsymptom development than the surfactant alone.

The data also suggests that the C₁₁EO7 alcohol may yield the bestbalance between stability and fast symptomology. As EO level increasesfrom 3-5-7, the EO3 alcohol solution separates into layers at roomtemperature, the EO5 to a lesser extent separates, while the EO7 andhigher containing formulations are homogeneous.

TABLE 3c Results of Greenhouse Efficacy Study of Experimental GlyphosateFormulations containing Nonionic Surfactants ± Pelargonic Acid ±Ammonium Sulfate on Lawn & Garden Weed Spectrum DIGSA POROL FESAR TRFRE1, 3, 7, 1, 3, 7, 14, 1, 3, 7, 1, 3, 7, 14, CODE 14, 21 DAT 21 DAT 14,21 DAT 21 DAT 998F3S 40, 73, 89, 52, 65, 73, 65, 79, 81, 66, 71, 72,non-foam 95, 98 90, 99 90, 91 83, 98 998F3S 50, 72, 82, 63, 78, 80, 67,81, 83, 62, 71, 76, Foaming 93, 94 92, 98 94, 98 90, 99 STD 2 38, 70,81, 70, 72, 76, 64, 75, 84, 75, 78, 79, non-foam 91, 91 89, 96 94, 9387, 95 STD 2 40, 68, 79, 65, 80, 83, 62, 77, 84, 60, 63, 71, foaming 94,95 96, 99 96, 97 75, 86 STD 3 62, 75, 75, 69, 80, 85, 52, 73, 79, 72,75, 78, 85, 93 92, 94 96, 98 89, 96 STD 7 5, 32, 53, 7, 42, 65, 2, 23,42, 13, 47, 75, 98, 100 88, 100 88, 100 95, 99 433S5C 63, 75, 79, 85,94, 98, 70, 85, 88, 82, 84, 83, 86, 91 98, 99 93, 94 84, 90 469A1T 65,82, 79, 85, 92, 99, 70, 88, 88, 82, 81, 79, 85, 88 99, 100 93, 93 83, 88469B8T 63, 80, 83, 83, 93, 97, 68, 88, 88, 80, 82, 79, 86, 93 98, 99 94,95 82, 89 480C5X 70, 83, 85, 80, 91, 98, 72, 87, 88, 81, 78, 75, 87, 8999, 100 95, 95 71, 80 483D2T 70, 81, 80, 79, 92, 96, 73, 87, 88, 87, 89,88, 87, 94 99, 98 94, 96 84, 83 495G6A 52, 75, 77, 69, 87, 84, 37, 68,69, 83, 86, 90, 89, 95 90, 90 85, 96 90, 98 475B6Y 69, 79, 79, 86, 91,99, 77, 87, 86, 83, 84, 82, 84, 91 99, 99 88, 92 84, 86 476K3W 58, 70,76, 73, 87, 83, 72, 85, 89, 75, 78, 81, 86, 90 92, 97 95, 96 91, 96513U9D 48, 65, 70, 70, 84, 86, 42, 66, 70, 72, 82, 82, 86, 90 90, 89 89,98 84, 93 471C9T 65, 75, 75, 82, 94, 98, 62, 78, 80, 77, 78, 80, 83, 88100, 99 85, 86 84, 89 471D3T 32, 42, 60, 45, 68, 73, 32, 57, 63, 63, 75,75, 96, 99 88, 95 90, 100 75, 95 474E7T 55, 65, 72, 71, 90, 93, 33, 66,71, 63, 69, 65, 87, 93 93, 93 89, 98 71, 82 420S8C 55, 65, 72, 68, 85,84, 43, 68, 72, 72, 75, 74, 88, 96 88, 90 92, 97 74, 80 435W6E 60, 67,72, 76, 83, 89, 60, 78, 80, 78, 81, 82, 87, 95 95, 98 85, 90 79, 89421L5N 55, 73, 75, 74, 89, 92, 48, 67, 73, 77, 79, 79, 89, 95 94, 97 88,90 78, 86 525R9B 60, 74, 77, 68, 85, 85, 55, 77, 80, 74, 79, 79, 86, 8992, 98 88, 93 79, 85 515N3B 70, 85, 86, 80, 91, 95, 70, 83, 83, 87, 89,85, 89, 96 97, 99 87, 92 85, 87 520C4X 65, 80, 80, 80, 93, 98, 63, 81,86, 82, 83, 83, 84, 85 99, 100 87, 83 82, 87 520W9S 63, 80, 83, 79, 91,96, 62, 80, 80, 81, 88, 87, 87, 95 97, 99 88, 88 85, 89 345R6C 48, 79,80, 68, 84, 79, 37, 64, 68, 80, 83, 80, 90, 97 83, 92 87, 98 80, 83350F1L 58, 68, 72, 81, 95, 99, 60, 77, 80, 80, 93, 90, 86, 89 100, 10083, 85 94, 95 235W9D 63, 78, 79, 82, 93, 96, 68, 82, 81, 83, 83, 84, 87,85 99, 100 81, 85 74, 86 240S8G 67, 77, 76, 83, 97, 99, 77, 88, 87, 82,83, 78, 82, 83 100, 100 93, 95 78, 83 240D3F 68, 72, 70, 85, 98, 100,70, 82, 82, 83, 88, 85, 78, 82 100, 100 89, 91 81, 83 675W3T 40, 60, 65,68, 78, 78, 42, 63, 69, 75, 84, 89, 93, 98 87, 93 88, 97 94, 98 245M9S63, 77, 75, 80, 94, 97, 70, 84, 84, 80, 86, 83, 83, 83 98, 100 89, 9480, 84

Discussion:

This test explored the efficacy advantage of formulations that containedTOMADOL 1-7 (linear C_(H) alcohol EO7) or NIS Surfactant with andwithout either pelargonic acid (PA) or ammonium sulfate (AMS). Also inthis test, the level of PA and AMS that would give the best overall fastsymptom development (1 DAT) was explored. Overall, the treatmentscontaining AMS gave better symptoms than treatments without AMS.

4. Field Study of Experimental and Commercial Glyphosate Formulations

Field studies were conducted using the compositions of the presentinvention. Compositions were prepared as in Tables 1.1-1.3. Eachcomposition as well as STD5, STD6 and STD7 were applied to the specieslisted below (Table 4.1) at a rate equivalent to 1348 liters per hectare(l/ha) with % control results reported in Tables 4.2a-4.2e.

Glyphosate formulations were applied post-emergence to all weed targets,generally when they were between about 8 cm and about 30 cm tall,depending on the species and the environmental conditions. Treated plotsize was generally 0.92 meters wide and 1.5 meters long. Treatments wereapplied with a two-gallon ROUNDUP pump up sprayer. Carrier volume wasequal to 1348 l/ha. A single Tee-Jet brand tapered flat fan spray tipwas used, at an appropriate spray pressure. Experimental design in eachstudy was randomized complete block design with three replications.

Weed control ratings were made by a single practiced technician, whorecorded percent control at various time points after treatment. Ratingswere based on quantitative visual estimates (0=no control, 10032completely dead, 85% threshold for commercial control). The effect ofthe formulation on the species in the treated plot was compared to thehealth and vigor of the species in the untreated buffer area immediatelyadjacent to the plot. Results are presented in Tables 4.2a-4.2e.

TABLE 4.1 Lawn & Garden Plants evaluated include the following; theseare exemplary, but not limiting. Bayer Code Common Name ANOSSbeardgrass, big bluestem sp. (Andropogon sp.) ASCLA milkweed, labriform(Asclepias labriformis Jones) CYNDA bermudagrass (Cynodon dactylon)DIORC Carolina dichondra DIGSA large crabgrass (Digitaria sanguinalis)DIGSO crabgrass, blanket (Digitaria serotina (Walt.) Michx.) EUPCPdogfenel (Eupatorium capillifolium (Lam.) small) FESAR tall fescue,(Festuca arundinacea Schreb); as turf grass FESAW tall fescue; as weedLIPNO lippia, mat (Nodiflora (L.) Greene) PASDI dallisgrass (Paspalumdilatatum) PASUR vesseygrass (Paspalum urvillei Steud.) PLALA buckhornplantain (Plantago lanceolata) POAPR kentucky bluegrass (Poa pratensisL.) POEPR rustweed (Polypremum procumbens) POROL common purslane(Portulaca oleracea) TTTTT total weeds, i.e., all weeds present TAROFcommon dandelion (Taraxacum officinale) TRFRE white clover (Trifoliumrepens) TRFPR red clover (Trifolium pratense) VEROF common speedwell(Veronica officinalis L.)

TABLE 4.2a Field Efficacy Study Results - Grand Summary NARROWLEAVES %BROADLEAVES % CONTROL AT CONTROL AT CODE 1, 3, 7, 14, DAT 1, 3, 7, 14,DAT 737F2S 48, 66, 80, 98 55, 68, 80, 97 022K8T 73, 85, 90, 99 72, 78,90, 99 451A2K 81, 90, 97, 100 82, 95, 97, 100 452B9X 73, 85, 96, 99 83,91, 96, 100 453C7P 86, 94, 97, 99 85, 95, 97, 100 454D4K 82, 90, 94, 9981, 92, 94, 100 455E8S 79, 91, 92, 99 76, 86, 92, 99 456F6H 69, 86, 89,99 65, 77, 89, 99 457G1T 37, 67, 84, 99 43, 66, 84, 97 998F3S 61, 79,82, 99 61, 70, 82, 99 STD6 35, 82, 92, 97 44, 83, 92, 99 STD7 1, 21, 67,98 2, 22, 67, 100 STD5 85, 99, 99, 96 93, 100, 99, 98

Discussion:

These data show that the formulations that contain 2% PA yield betterearly symptom development than formulations that contain 1 and 0.4% PA.Also that the formulations that contains NIS yield greater than earlysymptom development than no NIS, particularly when combined with PA andAMS. Lastly, the formulations that contain AMS yield better earlysymptom development than formulations with 1% AMS (or 2.6% AmmoniumNitrate) which have better development than no AMS.

TABLE 4.2b Results of Field Efficacy Study of Standard and ExperimentalGlyphosate Formulations - Detailed Summary SPECIES MEANS AT 1, 3/4, 7,14 DAT CODE FESAR POAPR TRFPR VEROF CYNDA DIGSO EUPCP POEPR 737F2S 18,35, 48, 83, 88, 92, 85, 92, 65, 72, 50, 87, 47, 83, 53, 90, 69, 100 88,100 96, 99 96, 100 88, 96 100, 100 100, 100 100, 100 998F3S 30, 61, 75,95, 86, 92, 85, 96, 65, 75, 67, 90, 73, 97, 87, 100, 82, 100 96, 100 98,100 98, 100 85, 98 100, 100 100, 100 100, 100 022K8T 52, 75, 78, 96, 88,97, 88, 97, 68, 77, 100, 100, 100, 100, 100, 100, 93, 100 97, 100 97, 9997, 100 88, 99 100, 100 100, 100 100, 100 451A2K 60, 79, 84, 97, 91, 97,91, 99, 88, 91, 90, 90, 73, 93, 100, 100, 93, 100 98, 100 99, 100 99,100 97, 99 100, 100 100, 100 100, 100 452B9X 43, 62, 68, 94, 88, 99, 90,99, 85, 91, 77, 87, 90, 90, 100, 100, 93, 100 97, 100 99, 100 99, 10096, 99 100, 100 100, 100 100, 100 453C7P 68, 86, 83, 98, 91, 99, 92, 99,92, 94, 93, 100, 100, 100, 100, 100, 97, 100 97, 100 96, 98 96, 100 96,98 100, 100 100, 100 100, 100 454D4K 60, 81, 88, 98, 92, 100, 90, 100,83, 87, 93, 100, 100, 100, 100, 100, 95, 100 99, 100 100, 100 100, 10094, 97 100, 100 100, 100 100, 100 455E8S 66, 86, 85, 99, 91, 100, 90,100, 76, 84, 97, 100, 100, 100, 100, 100, 95, 100 99, 100 98, 97 98, 10091, 99 100, 100 100, 100 100, 100 456F6H 61, 85, 72, 96, 87, 99, 87, 98,70, 77, 70, 87, 83, 90, 97, 100, 95, 100 99, 100 98, 97 98, 100 87, 99100, 100 100, 100 100, 100 457G1T 29, 62, 50, 81, 68, 91, 70, 90, 46,62, 20, 77, 17, 43, 60, 100, 87, 100 93, 100 98, 100 98, 100 80, 97 100,100 90, 100 100, 100 STD 6 29, 79, 17, 86, 33, 93, 38, 93, 48, 84, 47,100, 0, 90, 40, 100, 91, 98 94, 98 95, 98 95, 100 94, 95 100, 100 100,100 100, 100 STD 7 2, 12, 3, 40, 2, 47, 2, 47, 2, 16, 0, 23, 0, 0, 0,17, 55, 99 84, 100 94, 100 94, 100 67, 97 100, 100 80, 100 50, 100 STD 574, 99, 57, 98, 73, 98, 70, 98, 97, 99, 100, 100, 100, 100, 100, 100,99, 99 99, 97 96, 95 96, 100 99, 95 100, 100 100, 100 100, 100 SPECIESMEANS AT 1, 3/4, 7, 14 DAT GRAND CODE LIPNO PASUR FESAW PASDI ANDGLASCLA DICCA MEAN 737F2S 33, 20, 67, 100, 18, 47 81, 87, 73, 80, 65, 80,5, 12, 51, 67, 50, 100 100, 100 89, 97 74, 100 0, 100 25, 73 83, 98998F3S 40, 20, 80, 100, 70, 91 89, 95, 28, 45, 80, 90, 5, 7, 61, 75, 50,100 100, 100 96, 99 82, 100 0, 100 28, 88 86, 99 022K8T 57, 50, 87, 100,82, 93 97, 97, 57, 83, 0, 0, 0, 5, 12, 72, 82, 87, 100 100, 100 97, 9997, 99 100 25, 93 92, 99 451A2K 60, 83, 87, 100, 82, 92 94, 95, 92, 95,96, 100, 54, 92, 81, 92, 90, 100 100, 100 94, 100 100, 100 0, 100 84,100 97, 100 452B9X 90, 100, 90, 100, 77, 92 92, 97, 85, 83, 93, 100, 28,55, 77, 87, 100, 100 100, 100 95, 99 98, 99 0, 100 70, 99 96, 100 453C7P90, 100, 100, 100 87 96 95, 98, 92, 90, 90, 98, 31, 71, 86, 94, 100, 100100, 100 98, 99 99, 100 0, 100 87, 99 97, 99 454D4K 87, 100, 100, 100,88, 96 99, 97, 72, 90, 90, 0, 20, 52, 81, 91, 100, 100 100, 100 98, 99100, 100 0, 100 40, 97 95, 99 455E8S 87, 100, 90, 100, 83, 95 95, 97,42, 70, 87, 95, 11, 18, 78, 89, 100, 100 100, 100 98, 99 80, 100 0, 10045, 95 94, 99 456F6H 77, 100, 90, 100, 42, 90 89, 96, 17, 43, 0, 0, 0,7, 12, 67, 83, 100, 100 100, 100 97, 99 70, 100 100 30, 93 92, 99 457G1T53, 83, 30, 90, 18, 43 62, 77, 21, 28, 48, 73, 2, 8, 39, 67, 100, 100100, 100 92, 99 47, 97 0, 100 33, 80 86, 98 STD 6 43, 27, 43, 100, 18,83 13, 42, 63, 73, 58, 95, 100, 95, 38, 82, 63, 100 100, 100 87, 98 92,98 0, 100 100, 100 93, 98 STD 7 0, 10, 0, 40, 0, 20 3, 23, 5, 28, 5, 18,3, 11, 2, 21, 33, 100 100, 100 80, 99 58, 100 0, 100 45, 100 71, 99 STD5 100,100, 100,100, 67, 97 88, 94, 98, 100, 100,100, 99, 100, 88, 99,100, 100 100, 100 92, 86 100, 99 0, 100 100, 90 99, 97

TABLE 4.2c Results of Field Efficacy Study of Standard and ExperimentalGlyphosate Formulations TRFRE FESAR POAPW PLALA TTTTT SPECIES MEANS AT1, 5 & 9 HAT (HOUR AFTER TREATMENT) CODE AND 1, 2, 5, 8, 14, 29 DATrespectively 295L1V 3, 63, 62, 0, 7, 27, 0, 15, 33, 10, 20, 40, 5, 37,48, 68, 76, 82, 32, 45, 45, 40, 53, 55, 48, 52, 47, 55, 55, 62, 91, 100,99, 100, 99, 100, 98, 100, 96, 100, 100 100 100 100 100 451A2K 3, 87,89, 0, 18, 28, 0, 38, 50, 10, 81, 94, 7, 72, 73, 94, 95, 94, 58, 77, 77,79, 91, 90, 98, 94, 90, 84, 87, 88, 91, 99, 100 99, 100, 99, 100, 99,100, 96, 99, 100 100 100 100 453C7P 8, 91, 95, 3, 53, 88, 3, 75, 90, 22,91, 97, 10, 84, 91, 98, 98, 97, 92, 94, 91, 97, 97, 97, 99, 95, 95, 95,95, 95, 92, 100, 100, 100, 100, 100, 100, 100, 97, 100, 100 100 100 100100 STD 8 0, 3, 7, 0, 0, 7, 0, 3, 7, 0, 2, 10, 0, 3, 7, 33, 35, 47, 17,23, 20, 17, 28, 38, 33, 28, 40, 25, 28, 43, 98, 100, 99, 100, 99, 100,70 99, 100, 98, 100, 100 100 100 100

TABLE 4.2d Results of Field Efficacy Study of Standard and ExperimentalGlyphosate Formulations - cont. TRFRE DIORC CYNDA PLALA TTTTT SPECIESMEANS AT 1, 5 & 9 HAT (HOUR AFTER TREATMENT) CODE AND 1, 3, 7, 14, 28DAT 295L1V 18, 30, 33, 15, 18, 23, 12, 17, 18, 8, 18, 15, 18, 30, 33,40, 58, 68, 25, 30, 38, 17, 20, 25, 28, 20, 30, 40, 47, 59, 69, 73 67,92 89, 90 100 70, 69 451A2K 23, 35, 40, 18, 22, 30, 13, 20, 30, 28, 48,53, 23, 38, 42, 47, 70, 75, 38, 42, 55, 35, 40, 43, 53, 58, 55, 50, 58,68, 75, 78 76, 95 92, 84 100 79, 72 453C7P 28, 45, 20, 33, 45, 15, 40,48, 30, 58, 64, 32, 48, 52, 47, 55, 48, 52, 62, 52, 62, 65, 68, 79, 79,61, 68, 74, 76, 69, 87, 97 93, 71 100 73, 69 71, 72 STD 8 0, 2, 13, 0,5, 8, 10, 2, 10, 0, 0, 8, 0, 3, 15, 17, 23, 20, 22, 35, 20, 15, 25, 20,18, 30, 18, 23, 52, 48, 75, 88 68, 95 92, 87 94 78, 81

Discussion:

The field tests in Tables 4.2c-4.2d show data comparing formulationswith No PA (STD8), PA alone (295L1V), PA+AMS (451A2K) and PA+AMS+NIS(453C7P). The data clearly shows the benefit of PA to fast symptomdevelopment over no PA. Also noted is the advantage to fast symptomdevelopment when AMS is added to the formulation. The advantage overallto the formulation containing all three components (PA+AMS+NIS) isevident.

TABLE 4.2e Results of Field Efficacy Study of Standard and ExperimentalGlyphosate Formulations - with or without Imazapic FESAR POAPW TRFRETAROF TTTTT TTTTT 1, 3, 7, 1, 3, 7, 1, 3, 7, 1, 3, 7, 1, 3, 7, % weedfree at 31, 46, 60, and CODE 15, 31 DAT 15, 31 DAT 15, 31 DAT 15, 31 DAT15, 31 DAT 90 DAT respectively 295L1V 52, 77, 85, 75, 91, 90, 88, 84,80, 78, 87, 80, 80, 86, 82, 93, 62, 5, 4 97, 100 99, 100 83, 92 89, 10088, 96 451A2K 90, 83, 90, 95, 96, 95, 88, 87, 82, 89, 86, 81, 92, 91,86, 92, 67, 37, 0 98, 100 98, 100 86, 88 91, 100 91, 93 489H1P 91, 89,93, 95, 95, 97, 95, 92, 88, 92, 90, 90, 95, 94, 94, 94, 98, 97, 89 98,100 99, 100 87, 88 94, 100 93, 94 490K9E 87, 88, 89, 95, 96, 95, 89, 87,77, 88, 88, 79, 92, 90, 86, 84, 91, 91, 62 97, 100 99, 100 78, 79 91,100 85, 87

Discussion:

This test demonstrates that adding imazapic as an active ingredient intothis type of formulation does not interfere with the fast symptomdevelopment when the formulation contains either (PA+AMS) or(PA+AMS+NIS).

5. Study of the effect of pH on efficacy of glyphosate Formulations

Experimental formulations were prepared at different pH values as inTable 5.1 and were evaluated under Greenhouse Study protocols aspreviously described. The results are summarized in Table 5.2. Datareported is % control at 1, 3, 6 Hours after treatment (HAT) and 1, 3,7, 14, 24 DAT, respectively, for each species (treated vs. untreatedcontrol).

TABLE 5.1 Glyphosate Formulations Prepared to Demonstrate pH Effect onEfficacy of the Formulation Example 1 2 3 4 5 6 pH 7.1 pH 7.3 pH 7.4 pH7.5 pH 7.6 pH 7.8 Component Weight of component (g) 62% solution of IPA32.2 32.2 32.2 32.2 32.2 32.2 Glyphosate TOMADOL 1-7 15 15 15 15 15 15Antimicrobial (OTH2) 1 1 1 1 1 1 Pelargonic Acid 20 20 20 20 20 20 45%KOH 21.5 22.8 23.4 24 24.3 25.1 Ammonium Sulfate 20 20 20 20 20 20Antifoam (OTH3) 0.1 0.1 0.1 0.1 0.1 0.1 Water 892 889 888.4 887.9 887.5886.6 Total 1001.8 1000.1 1000.1 1000.2 1000.1 1000

TABLE 5.2 Results of Greenhouse Efficacy Study of ExperimentalGlyphosate Formulations at varied pH DIGSA POROL FESAR TRFRE at 1, 3, 6Hours (HAT) and 1, 3, 7, 14, 24 days (DAT) respectively for FormulationpH each species 1 7.1 35, 50, 32, 48, 15, 40, 62, 73, 65, 89, 60, 78,57, 70, 77, 79, 97, 97, 73, 77, 82, 82, 82, 73, 95, 97 83, 84 83, 92 73,70 2 7.3 40, 45, 38, 50, 13, 38, 62, 73, 57, 87, 67, 72, 53, 65, 73, 76,93, 94, 73, 85, 79, 85, 83, 72, 98, 99 95, 100 92, 99 68, 62 3 7.4 35,40, 37, 50, 12, 30, 62, 73, 50, 85, 60, 70, 48, 63, 77, 76, 86, 90, 77,80, 73, 78, 78, 69, 98, 98 92, 98 84, 97 67, 55 4 7.5 37, 43, 32, 45,15, 72, 63, 72, 52, 78, 52, 72, 42, 60, 74, 77, 80, 83, 70, 80, 73, 81,81, 73, 93, 100 91, 97 85, 97 68, 73 5 7.6 38, 43, 35, 45, 13, 35, 63,70, 50, 85, 58, 75, 50, 71, 75, 75, 88, 90, 70, 80, 78, 87, 79, 68, 95,97 87, 96 91, 99 65, 60 6 7.8 38, 45, 37, 50, 18, 35, 63, 70, 53, 89,60, 72, 53, 72, 75, 77, 91, 90, 75, 84, 78, 88, 81, 72, 98, 98 94, 9993, 95 63, 60

Discussion:

The greenhouse data in Table 5.2 show data comparing formulationscontaining 2% IPA glyphosate, 2% PA, 2% AMS, 1.5% NIS with pH variedfrom 7.1 to 7.8. The data clearly shows that there is no effect in thefast symptom development or long term control on any of the test speciesas the pH changes.

6. Study of the Effect of Ammonium Sulfate on Efficacy of Glyphosateformulations with varying pH

Experimental formulations were prepared at different pH values with orwithout ammonium sulfate as in Table 6.1 and were evaluated underGreenhouse Study protocols as previously described. The results aresummarized in Table 6.2. Data reported is % control at 1, 3, 7, 14, 21DAT, respectively, for each species (treated vs. untreated control).

TABLE 6.1 Glyphosate Formulations Prepared to Demonstrate pH Effect,with or without Ammonium Sulfate, on Efficacy of the FormulationFormulations with ammonium sulfate Example 1a 2a 3a 4a pH 7.0 pH 7.2 pH7.4 pH 7.6 Component Weight of component (g) 62% IPA Glyphsoate 32.232.2 32.2 32.2 solution Surfactant (SUB2) 5 5 5 5 Antimicrobial (OTH2) 11 1 1 Pelargonic Acid 20 20 20 20 45% KOH 24.2 25.1 28.1 29.6 AmmoniumSulfate 20 20 20 20 Antifoam (OTH3) 0.1 0.1 0.1 0.1 Water 897.5 896.6893.8 891.4 Total 1000.0 1000.0 1000.2 999.3 Formulations withoutammonium sulfate Example 1b 2b 3b 4b pH 7.0 pH 7.2 pH 7.4 pH 7.6Component Weight of component (g) 62% IPA Glyphsoate 32.3 32.3 32.3 32.3solution Surfactant (SUB2) 5 5 5 5 Antimicrobial (OTH2) 0.3 0.3 0.3 0.3Pelargonic Acid 20 20 20 20 45% KOH 25.0 26.3 28.5 29.6 Propylene Glycol6.6 6.6 6.6 6.6 Water 912.9 909.6 907.2 906.3 Total 1002.9 1000.1 999.91000.1

TABLE 6.2 Results of Greenhouse Efficacy Study of ExperimentalGlyphosate Formulations at varied pH DIGSA POROL FESAR TRFRE FormulationpH at 1, 3, 7, 14, 21 DAT respectively 1a 7.0 76, 77, 75, 85, 65, 74,65, 75, 81, 79, 83, 89, 77, 78, 75, 72, 93 100 90 85 2a 7.2 76, 75, 73,84, 67, 85, 68, 73, 84, 95, 90, 98, 93, 100, 85, 97, 100 100 100 100 3a7.4 80, 82, 72, 81, 69, 88, 63, 69, 88, 96, 88, 99, 93, 100, 83, 97, 100100 100 98 4a 7.6 79, 80, 77, 85, 74, 93, 65, 66, 88, 94, 93, 99, 97,100, 78, 88, 99 100 100 98 1b 7.0 73, 74, 63, 70, 65, 75, 65, 66, 87,97, 85, 98, 86, 97, 73, 81, 100 100 100 94 2b 7.2 73, 70, 52, 55, 69,81, 60, 65, 81, 92, 76, 93, 90, 100, 75, 87, 99 100 100 94 3b 7.4 62,63, 50, 52, 60, 68, 62, 64, 72, 78, 76, 98, 86, 98, 72, 82, 93 100 10095 4b 7.6 62, 67, 42, 47, 53, 63, 65, 71, 75, 77, 62, 76, 78, 85, 77,81, 90 98 97 98

Discussion:

Table 6.2 shows the data from a greenhouse test of the formulationslisted in Table 6.1. The data clearly demonstrates that formulations1b-4b show slower development of symptoms as the pH rises from 7.0 to7.6. The formulations 1a-4a show little to no effect in fast symptomdevelopment as the pH rises. The data also demonstrates thatformulations 1a-4a generally give much better control particularly at 1and 3 DAT than formulations 1b-4b.

The present invention is not limited to the above embodiments and can bevariously modified. The above description of the preferred embodiments,including the Examples, is intended only to acquaint others skilled inthe art with the invention, its principles, and its practicalapplication so that others skilled in the art may adapt and apply theinvention in its numerous forms, as may be best suited to therequirements of a particular use.

With reference to the use of the word(s) comprise or comprises orcomprising in this entire specification (including the claims below),unless the context requires otherwise, those words are used on the basisand clear understanding that they are to be interpreted inclusively,rather than exclusively, and that each of those words is to be sointerpreted in construing this entire specification.

1. An aqueous herbicidal composition useful for killing or controllingthe growth of unwanted plants, comprising: a glyphosate componentcomprising N-(phosphonomethyl)glycine, an agronomically acceptable saltof N-(phosphonomethyl)glycine or a mixture thereof; a fatty acidcomponent comprising at least one saturated or unsaturated, straight orbranched chain C₅ to C₁₈ fatty acid or agronomically acceptable saltthereof; and a nonionic surfactant component comprising an alkoxylated,C₈ to C₂₀, nonaromatic alcohol with an average degree of alkoxylationsuch that the alcohol has a solubility in water of at least about 0.5%by weight at 25° C.
 2. The herbicidal composition according to claim 1wherein the alkoxylated, C₈ to C₂₀, nonaromatic alcohol has an averagedegree of alkoxylation of from about 2 to about
 20. 3. The herbicidalcomposition according to claim 2 wherein the nonionic surfactantcomponent comprises an ethoxylated, C₈ to C₂₀, nonaromatic alcohol withan average degree of ethoxylation from about 3 to about
 12. 4. Theherbicidal composition according to claim 3 wherein the nonionicsurfactant component comprises an ethoxylated, primary or secondary,linear or minimally branched C₁₀ to C₁₄ alcohol having no more than 2methyl substituents and an average degree of ethoxylation of from about5 to about
 9. 5. The herbicidal composition according to claim 4 whereinthe nonionic surfactant component predominantly comprises ethoxylated,primary or secondary, undecyl alcohol with an average degree ofethoxylation of from about 5 to about
 9. 6. The herbicidal compositionaccording to claim 5 wherein the undecyl alcohol that predominates thenonionic surfactant component is ethoxylated, primary, linear undecylalcohol.
 7. The herbicidal composition according to claim 6 wherein thenonionic surfactant component comprises at least about 90% by weightethoxylated, primary, linear undecyl alcohol having an average degree ofethoxylation of about
 7. 8. The herbicidal composition according toclaim 1 wherein the fatty acid component predominantly comprises atleast one C₈ to C₁₂ saturated, straight or branched chain fatty acid oragronomically acceptable salt thereof.
 9. The herbicidal compositionaccording to claim 8 wherein the fatty acid component predominantlycomprises pelargonic acid or an agronomically acceptable salt thereof.10. The herbicidal composition according to claim 9 wherein the fattyacid component comprises at least about 90% by weight pelargonic acid oran agronomically acceptable salt thereof.
 11. The herbicidal compositionaccording to claim 1 wherein the glyphosate component predominantlycomprises an agronomically acceptable salt ofN-(phosphonomethyl)glycine.
 12. The herbicidal composition according toclaim 11 wherein the glyphosate component predominantly comprises a saltof N-(phosphonomethyl)glycine selected from the potassium, monoammonium,diammonium, sodium, monoethanolammonium, n-propylammonium,isopropylammonium, ethylammonium, dimethylammonium, ethylenediamine,hexamethylenediamine and trimethylsulfonium salts ofN-(phosphonomethyl)glycine and combinations thereof.
 13. The herbicidalcomposition according to claim 1 wherein the composition furthercomprises an agronomically acceptable inorganic ammonium salt.
 14. Theherbicidal composition according to claim 13 wherein the agronomicallyacceptable inorganic ammonium salt is selected from the group consistingof ammonium sulfate, ammonium nitrate, ammonium thiocyanate, ammoniumphosphate, ammonium chloride and mixtures thereof.
 15. The herbicidalcomposition according to claim 14 wherein the composition comprisesammonium sulfate.
 16. The herbicidal composition according to claim 1comprising at least about 0.1% by weight (a.e.) of the glyphosatecomponent, at least about 0.25% by weight (a.e.) of the fatty acidcomponent and at least about 0.5% by weight of the nonionic surfactantcomponent.
 17. The herbicidal composition according to claim 16 in theform of a ready-to-use herbicidal composition, the ready-to-useherbicidal composition comprising from about 0.1% to about 5% by weight(a.e.) of the glyphosate component, from about 0.25% to 5% by weight(a.e.) of the fatty acid component and from about 0.5% to about 12% byweight of the nonionic surfactant component.
 18. The ready-to-useherbicidal composition according to claim 17 comprising from about 1% toabout 2% by weight (a.e.) of the glyphosate component, at least about1.5% and up to about 3% by weight (a.e.) of the fatty acid component andfrom about 0.5% to about 5% by weight of the nonionic surfactantcomponent.
 19. The ready-to-use herbicidal composition according toclaim 17 further comprising one or more ingredients selected from thegroup consisting of additional herbicidal active ingredients,foam-moderating agents, preservatives, antifreeze agents,solubility-enhancing agents, dyes, pH adjusters and thickening agents.20. The ready-to-use herbicidal composition according to claim 19wherein the additional herbicidal active ingredient is selected fromwater-soluble forms of (2,4-dichlorophenoxy)acetic acid (2,4-D),4-(2,4-dichlorophenoxy)butanoic acid (2,4-DB),(4-chloro-2-methylphoenoxy)acetic acid (MCPA), dicamba, diquat bromide,glufosinate, imazapic, imazapyr, imazethapyr, triclopyr and mixturesthereof.
 21. The herbicidal composition according to claim 16 in theform of a herbicidal concentrate composition, the herbicidal concentratecomposition comprising from about 5% to about 25% by weight (a.e.) ofthe glyphosate component, from about 2% to 25% by weight (a.e.) of thefatty acid component and from about 5% to about 50% by weight of thenonionic surfactant component.
 22. The herbicidal concentratecomposition according to claim 21 wherein the glyphosate componentpredominantly comprises a salt of N-(phosphonomethyl)glycine selectedfrom the isopropylammonium salt of N-(phosphonomethyl)glycine, theammonium salt of N-(phosphonomethyl)glycine, the potassium salt ofN-(phosphonomethyl)glycine and combinations thereof.